Exp173

=Objective= To synthesize a 16 Ugi adducts using Ugi 4CR following Explan005 .The target compound were ranked [|13-30] in the [|DEXP014-V2B] file from D-EXP014. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this [|summary post]. =Procedure= To sixteen vials, labeled 13-29) (except 23) and charged with methanol, four reactants [aldehyde, amine, acid and isocyanide] (1mmol each) were added to each in that order. After each addition, the resulting solution was vortexed for 15s (or more) and confirmed that a homogeneous solution had been obtained. The vials were capped tight and left at room temperature. After crystallization, the solution was decanted and the solid was washed with methanol (3x 500uL, and dried under vacuum to obtain corresponding di-amides
 * [|173B/14]** **N-[2-(tert-butylamino)-2-oxo-1-(p-tolyl)ethyl]-N-methyl-4-pyren-1​-yl-butanamide**: C34H36N2O2; White solid; M.Pt- 140-142C; 1H NMR ([[image:http://pubs.acs.org/images/gifchars/delta.gif]] ppm, 500MHz, CDCl3) 1.35 (s, 9H), 2.16-2.28 (m, 2H), 2.30 (s, 3H), 2.36-2.45 (m, 1H), (2.46-2.60 (m, 1H), 2.76 (s, 3H), 3.38 (ddd, 2H J=9.3, 6.5, 7.5Hz), 5.71 (bs, 1H), 6.24 (s, 1H), 7.14 (d, 2H, J=8.0Hz), 7.21 (d, 2H, J=8.0Hz), 7.82 (d, 1H, J=7.7Hz), 7.90-8.20 (m, 7H), 8.30 (d, 1H, J=9.3Hz); 13C NMR ([[image:http://pubs.acs.org/images/gifchars/delta.gif]] ppm, CDCl3) 20.8, 26.5, 28.5, 32.2, 32.5, 32.8, 51.3, 60.1, 123.2, 124.4, 124.5, 124.7, 124.8, 125.5, 126.3, 127.0, 127.1, 127.2, 128.5, 128.9, 129,2, 129.6, 130.6, 131.1, 132.7, 136.0, 137.7, 169.3, 173.2; HRMS (FAB,//m-//nitrobenzyl alcohol): //m/z// calcd for C34H36N2O2Na (M+Na) 527.2674 Da, found 527.2667 Da; yield 46%
 * [|173G19-4]** **N-benzyl-N-[2-butylamino-1-(3,5-dimethoxyphenyl)-2-oxo-ethyl]-3-p​henyl-prop-2-ynamide**: C30H32N2O4; White solid; M.Pt-137-139C; 1H NMR ([[image:http://pubs.acs.org/images/gifchars/delta.gif]] ppm, 500MHz, CDCl3); listed NMR peaks are common to both rotamers (E, Z) unless otherwise stated; rotamers are denoted by major and minor and are present in a 3:1 ratio at rt) 0.79 (t, 3H, J=7.3 Hz, //minor//), 0.88 (t, 3H, J= 7.3Hz, //major//), 1.13-1.23 (m, 2H, //minor//), 1.24-1.33 (m, 2H, //major//), 1.37-1.50 (m, 2H), 3.12-1.24 (m, 1H), 3.23-3.34 (m, 1H), 3.65 (s, 6H, //major//), 3.66 (s, 6H, //minor//), 4.59 (d, 1H, J= 15.1Hz, //minor//), 4.66 (d, 1H, J= 15.1Hz, //minor//), 4.78 (d, 1H, J= 16.6 Hz, //major//), 5.14 (d, 1H, J= 16.6 Hz, //major//), 5.68 (s, 1H, //major//), 5.97 (t, 1H, J= 5.8Hz, //minor//), 6.04 (t, 1H, J= 5.8Hz, //major//), 6.12 (s, 1H, //minor//), 6.29-6.34 (m, 1H, //major//), 6.35-6.37 (m, 1H, //minor//), 6.40 (d, 1H, J=2.4Hz), //minor//),6.43 (d, 1H, J=2.4Hz, //major//), 7.09 (dd, 1H, J= 7.8, 1.4Hz), 7.14-7.23 (m, 5H), 7.24-7.31 (m, 2H), 7.32-7.48 (m, 2H), 7.56 (d,H, J= 7.8Hz); 13C NMR ([[image:http://pubs.acs.org/images/gifchars/delta.gif]] ppm, CDCl3 / CD3OD) 13.11//(minor),// 13.17//(major),// 19.60, 30.79//(major),// 30.85//(minor),// 39.01//(major),// 39.06//(minor),// 47.26, 51.45, 54.87//(major),// 54.91//(minor),// 62.25//(major),// 66.32//(minor)//, 80.80//(minor),// 81.39//(major),// 91.40//(major),// 92.70//(minor),// 100.50//(minor),// 100.55//(major),// 107.54//(major),// 107.60//(minor),// 119.50//(minor),// 119.53//(major)//, 126.55//(major),// 126.65//(minor),// 127.34, 127.71//(minor),// 127.78//(major),// 128.16//(major),// 128.27//(minor),// 130.06//(major),// 130.25//(minor),// 132.08//(major),// 132.23//(minor),// 135.50//(major),// 135.54//(minor),// 137.10//(major),// 137.50//(minor),// 156.16//(minor),// 156.29//(major),// 160.44//(major),// 160.56//(minor)// 168.78//(major),// 168.95//(minor).// HRMS (FAB,//m-//nitrobenzyl alcohol): //m/z// calcd for C30H32N2O4Na (M+Na) 507.2259 Da, found 507.2247 Da; yield 44%

VB2Rank || Solvent Methanol || Aldehyde || Amine || Acid || Isocyanide || Ppt(Y/N) & Yield || (1mmol,106.6uL) || Aniline (1mmol,91.1uL) || 4-chlorophenylacetic acid (1mmol,170.6mg) || Tosylmethylisocyanide (1mmol, 195.24mg) || **N** || (1mol,118uL) || Methylamine (1mmol,500uL) || 1-Pyrenebutanoic acid (1mmol,288.3mg) || t-butylisocyanide (1mmol,113.1uL) || ** Y ** (1mmol,136.5uL) || Methylamine (1mmol,500uL) || 1-Pyrenebutanoic acid (1mmol, 288.3mg) || t-butylisocyanide (1mmol, 113.1uL) || Reactants insoluble under the conditions || (1mmol, 106.5uL) || Methylamine (1mmol, 500uL) || 1-Pyrenebutanoic acid (1mmol, 288.3mg) || n-Butylisocyanide (1mmol,104.5uL) || Reactants insoluble under the conditions || (1mmol, 138.1mg) || Methylamine (1mmol, 500uL) || Boc-tryptophan (1mmol, 304.3mg) || t-butylisocyanide (1mmol, 113.1uL) || **N** || (1mmol, 206.2mg) || Furfurylamine (1mmol, 88.3uL) || 2,3-dihydroxybenzoic acid (1mmol, 1)154.1mg || t-butylisocyanide (1mmol, 113.1uL) || **N** || (1mmol, 166.2mg) || Benzylamine (1mmol,109.2uL) || Phenylpropynoic acid (1mmol, 146.1mg) || n-Butylisocyanide (1mmol, 104.5uL) || ** Y ** (1mmol, 156.2mg) || 5-Methyl furfurylamine (1mmol,111.5uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || **N** || (1mmol, 122.1mg) || Methylamine (1mmol, 500uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || **N** || (1mmol, 138.1mg) || Methylamine (1mmol, 500uL) || 1-Pyrenebutanoic acid (1mmol,288.3mg) || t-butylisocyanide (1mmol, 113.1uL) || Reactants insoluble under the conditions || (1mmol, 122.1mg) || Furfurylamine (1mmol, 88.4uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || **N** || (1mmol, 140.5mg) || Furfurylamine (1mmol, 88.4uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || **N** || (1mmol, 152.1mg) || 2-Chloroaniline (1mmol,105.2uL) || decanoic acid (1mmol, 192.9mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || Waiting Analysis || (1mmol, 101.5uL) || Furfurylamine (1mmol, 88.4uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || ** Y ** || (1mmol, 121.9uL) || Methylamine (1mmol, 500uL) || 1-Pyrenebutanoic acid (1mmol,288.3mg) || t-butylisocyanide (1mmol, 113.1uL) || Reactants insoluble under the conditions || (1mmol, 118uL) || Furfurylamine (1mmol, 88.4uL) || 3,4-dihydroxy phenylacetic acid (1mmol, 168.1mg) || Tosylmethylisocyanide (1mmol, 195.2mg) || **N** || Compounds ranked 23 and 30 will be synthesized at a later date - 4-hydroxybenzaldehyde is not available at this time.
 * ExpID/
 * 173A/13 || Methanol || 2-hydroxybenzaldehyde
 * 173B/14 || Methanol || 4-methylbenzaldehyde
 * Yield 46%** ||
 * 173C/15 || Methanol || 4-(trifluoromethyl)benzaldehyde
 * 173D/16 || Methanol || 2-hydroxybenzaldehyde
 * 173E/17 || Methanol || 3,4-dihydroxybenzaldehyde
 * 173F/18 || Methanol || Phenanthrene-9-carbaldehyde
 * 173G/19 || Methanol || 3,5-dimethoxybenzaldehyde
 * Yield 44%** ||
 * 173H/20 || Methanol || 2-Naphthaldehyde
 * 173I/21 || Methanol || 3-hydroxybenzaldehyde
 * 173J/22 || Methanol || 3,4-dihydroxybenzaldehyde
 * 173L24 || Methanol || 3-hydroxybenzaldehyde
 * 173M/25 || Methanol || 4-chlorobenzaldehyde
 * 173N/26 || Methanol || 2-hydroxy-3-methoxy benzaldehyde (o-vanillin)
 * 173O/27 || Methanol || Benzaldehyde
 * 173P/28 || Methanol || 3-methoxy benzaldehyde
 * 173Q/29 || Methanol || 4-methylbenzaldehyde

=Results=


 * Pictures taken soon after the addition of all reactants.**
 * 173A/13 || 173B/14 || 173C/15 || 173D/16 || 173E/17 || 173F/18 || 173G/19 || 173H/20 || 173I/21 || 173J/22 || 173L/24 || 173M/25 || 17N/26 || 173O/27 || 173P/28 || 173Q/29 ||
 * [[image:173A-13.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173A-13.JPG"]] || [[image:173B-14.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173B-14.JPG"]] || [[image:173C-15.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173C-15.JPG"]] || [[image:173D-16.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173D-16.JPG"]] || [[image:173E-17.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173E-17.JPG"]] || [[image:173F-18.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173F-18.JPG"]] || [[image:173G-19.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173G-19.JPG"]] || [[image:173H-20.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173H-20.JPG"]] || [[image:173I-21.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173I-21.JPG"]] || [[image:173J-22.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173J-22.JPG"]] || [[image:173L-24.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173L-24.JPG"]] || [[image:173M-25.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173M-25.JPG"]] || [[image:173N-26.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173N-26.JPG"]] || [[image:173O-27.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173O-27.JPG"]] || [[image:173P-28.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173P-28.JPG"]] || [[image:173Q-29.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173Q-29.JPG"]] ||
 * Pictures taken on the fifth day after the addition of all reactants**
 * 173A/13-2 || 173B/14-2 || 173C/15-2 || 173D/16-2 || 173E/17-2 || 173F/18-2 || 173G/19-2 || 173H/20-2 || 173I/21-2 || 173J/22-2 || 173L/24-2 || 173M/25-2 || 17N/26-2 || 173O/27-2 || 173P/28-2 || 173Q/29-2 ||
 * [[image:173A-13.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173A-2.JPG"]] || [[image:173B-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173B-2.JPG"]] || [[image:173C-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173C-2.JPG"]] || [[image:173D-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173D-2.JPG"]] || [[image:173E-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173E-2.JPG"]] || [[image:173F-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173F-2.JPG"]] || [[image:173G-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173G-2.JPG"]] || [[image:173H-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173H-2.JPG"]] || [[image:173I-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173I-2.JPG"]] || [[image:173J-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173J-2.JPG"]] || [[image:173L-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173L-2.JPG"]] || [[image:173M-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173M-2.JPG"]] || [[image:173N-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173N-2.JPG"]] || [[image:173O-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173O-2.JPG"]] || [[image:173P-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173P-2.JPG"]] || [[image:173Q-2.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173Q-2.JPG"]] ||

insoluble || Reactants insoluble || No Ppt || No Ppt || Crystals reported || Deep green coating on walls || No Ppt || Reactants insoluble || No Ppt || No Ppt || Ppt isolated || || Reactants insoluble || No Ppt || ** ISOLATED ** || Aborted || Aborted || Aborted || Aborted || 5th day ** ISOLATED ** || Aborted || Aborted || Aborted || Aborted || Aborted || 5th day ** ISOLATED ** || 9th day ** ISOLATED ** || Aborted || Aborted ||
 * Pictures taken if any significant changes were observed**
 * 173A/13-3 || 173B/14-3 || 173C/15-3 || 173D/16-3 || 173E/17-3 || 173F/18-3 || 173G/19-3 || 173H/20-3 || 173I/21-3 || 173J/22-3 || 173L/24-3 || 173M/25-3 || 17N/26-3 || 173O/27-3 || 173P/28-3 || 173Q/29-3 ||
 * No Ppt || [[image:173B14-7thday.JPG width="50" height="50" link="http://usefulchem.wikispaces.com/space/showimage/173B14-7thday.JPG"]] || Reactants
 * Aborted || 7th day

amount: 232 mg ; Yield- 46 % amount: 213 mg; Yield- 43.9 %
 * Characterization of** **[|173B14-4]**
 * 1) Melting Point :140-142C
 * 2) [|IR]
 * 3) [|HNMR(300MHz)]
 * 4) [|HNMR(500MHz)]
 * 5) [|HNMR] [H-Exchange with methanol-d4]
 * 6) [|Overlay] [with labile H Vs Exchanged]
 * 7) [|CNMR]
 * 8) [|FAB-MS] (Nominal Mass)
 * 9) [|FAB-MS] (HRMS)
 * Characterization of** **[|173G19-4]**
 * 1) Melting Point :137-139C
 * 2) [|IR]
 * 3) [|HNMR]
 * 4) [|HNMR] [H-Exchange with methanol-d4]
 * 5) [|Overlay][with labile H Vs Exchanged]
 * 6) [|CNMR]
 * 7) [|FAB-MS] (Nominal Mass)
 * 8) [|FAB-MS] (HRMS)

amount: 035 mg (Yield %)
 * Characterization of** **[|173O27-4]**
 * 1) Melting Point :176-178 C
 * 2) [|IR]
 * 3) [|HNMR]
 * 4) [|HNMR] [H-Exchange with methanol-d4]
 * 5) [|Overlay] [with labile H Vs Exchanged]
 * 6) [|CNMR]
 * 7) [|FAB-MS] (Nominal Mass)

=Discussion= Based on the images of 173B, it appears that all the undissolved starting material went into solution by day 5 then a precipitate formed on day 7 without any vortexing. This suggests that it is worth taking pictures every day to observe exactly how long the dissolution process took. //IR -// Shows the presence of carbonyl at 1624 cm-1, amide NH at 3318cm-1, etc. //NMR// - Proton NMR : A siglet corresponding to t-butyl (9H) is seen at 1.34 ppm, the region between 1.56 - 2.0 ppm is populated with a lot of signals, which may be attributed to the diastereotopic protons (from pyrene-butyric acid precursor) and one of the methyl groups (most likely one on benzene ring). This region some how integrates for more than 7 protons (expected)..this may either be due to instrument malfunction or impurities in the sample. A nice doublet of doublet of doublet integrating for 2H is seen at 3.31 ppm the coupling constants (9.3, 6.5 7.5Hz) and the location of the peak suggests that it corresponds to the diasterotopic CH2 connected to the pyrene ring...(see [|SDBS] # 6700). The chiral proton appears at 6.3 ppm and the amide NH at 5.94ppm.Yield 46%
 * **[|173B14-4 >]**

//IR// - Shows the presence of carbonyls at 1600 and 1632 cm-1, amide at 3274 cm-1 and C≡C stretch at 2222 cm-1. //NMR// - Proton NMR : Most peaks are duplicated, indicating the presence of [|(E/Z) rotamers]. This can be a result of rotation along a double bond formed by [|resonance] between N- and the carbon of the carbonyl group. Diasterotopic methylenes: The spectrum is further complicated by the diastereotopic nature of the CH2 groups of the n-butyl side chain and the benzylic CH2. Each proton of the diastereotopic CH2 next to the methyl group could in theory be a dddq (total 32 peaks), each proton of the following CH2 could be ddddd (total 32 peaks) and similarly a ddddd for each proton of the next CH2. Each proton of the benzylic methylene of each rotamer appears as dd (J=xxHz). However, since the n-butyl side chain is not very close to the chiral center, the splitting effect (magnetic non-equivalence) is not as pronounced consequently, a less complex spectrum. The enantiomeric (chiral) proton is seen as a singlet at 5.68 ppm. Rotamers : The two rotamers are in a ~3:1 ratio, a NOE experiment may be able to tell which of the two rotamers (E or Z) is more favored. The n-butyl side chain is seen for both the rotamers; for instance the terminal methyl group of the favored rotamer is seen at 0.88 ppm and for the other is seen at 0.79 ppm (in a ~ 3:1) ratio).. A similar duplication is seen for the benzylic CH2 groups. Yield 44%
 * **[|173G19-4]**

=Conclusion= Only two Ugi products were obtained.

=Log=

2008-02-24
13:00 Weighed all the solid aldehydes (1mmol). 14:00 Made up a solutions of all aldehydes (1mmol) in methanol. Vials requiring methylamine solution in methanol were added only 3500uL methanol (to make it even 4mL after the amine (500uL) addition) All other vials which use different amines were added 4mL of methanol. Vortexed each to make a homogenous solution, all aldehydes except phanthrene-9-carboxaldehyde dissolved in methanol. 15:35: Added respective amines to each aldehyde solution. Vortexed each solution to homogenize it. Obtained a picture [|after amine addition]. 18:50 It was noticed that vial 173N/26 (-//o//-vanillin, //o//-chloroaniline in methanol), previously clear, now formed crystals..(maybe the imine); even after vortexing for 3min the crystals did not dissolve.. 19:20 Weighed out all the acids and tosylmethyl isocyanide (1mmol,195.2mg **x** 8). 20:00 Started adding respective acids to the previously made aldehyde/amine solutions.Vortexed each solution. 21:26 Obtained a picture of the vials [|after acid addition]. The previously insoluble reactants from vial **173F/18** with Phenanthrene-9-carboxaldehyde and furfurylamine dissolved after the addition of 2,3-dihydroxybenzoic acid..ofcourse a little extra vortexing (4min) was required. Solutions to which 1-Pyrenebutanoic acid was added remained undissolved (**173B/14, 173C/15, 173D/16, 173J/22, 173P/28**). Apart from these, contents of vial **173N/26** remained undissolved after the addition of decanoic acid. 21:28 Started adding respective isocyanides to the vials. Vortexed for 15s...all the clear dissolved the isocyanides without any problem...the ones which had solid, still remained so...(previously mentioned six) 21:53 Obtained a picture of the vials [|after isocyanide additions].

2008-02-29
17:30 Obtained a picture of the vials (**all series -2 pics**) //**remember to vortex before taking pic in case solution supersaturated**// //**missing log entry for day 7 pics and observations**//

2008-03-04
13:30 Observed crystals in **173O/27**, obtained a picture.

2008-03-20
16:00 The methanolic solution from the crystalline products 173B/14, 173G/19 and 173O/27 was decanted. To the solid in the vials, methanol (1ml) was added, vortexed, transferred to a pre-weighed small vial and centrifuged. The supernatant was decanted. The solid was washed with methanol (2 x 1ml). A total of three methanol washes were performed. 19:40 The solid obtained after the decanting the supernatant was set under a high vac. 22:30 Removed the products from the high vac and stored them uncapped in a desiccator set under house vac. The products are now renamed as **173B/14-4, 173G/19-4, 173O/27-4**.

2008-03-21
14:30 Obtained
 * **173B/14-4** -- 232 mg
 * **173G/19-4** -- 213 mg
 * **173O/27-4** -- 035 mg

2008-03-23
14:52 Obtained HNMR of 173B/14-4 after dissolving it in CDCl3 (1ml) 18:00 Obtained CNMR of 17B/14-4.

2008-03-25
16:00 Obtained CNMR of 173G/19-4 18:00 Obtained CNMR of 173O/27-4 19:00 Decanted the solutions from the NMR tubes after adding methanol (1ml) to the NMR tubes (**173B/14-4, 173G/19-4, 173O/27-4**) in to a vial, evaporated the solvent and set them in a desiccator under a high vac. 21:00 Turned off the high vac and connected the high vac to house vac.

2008-03-26
11:00 The dry compounds were capped and stored back under vacuum.

2008-03-29
14:00 Tried to dissolve 173N in DMSO-d6..no success...[|IR]of 173N (130mg)

Tags

 * Compound || Inchi || InchiKey ||
 * [|2-hydroxybenzaldehyde] || [|InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H] || [|SMQUZDBALVYZAC]-[|UHFFFAOYAD] ||
 * 4-methylbenzaldehyde ||  ||   ||
 * 4-(trifluoromethyl)benzaldehyde ||  ||   ||
 * 3,4-dihydroxybenzaldehyde ||  ||   ||
 * Phenanthrene-9-carbaldehyde ||  ||   ||
 * 3,5-dimethoxybenzaldehyde ||  ||   ||
 * 2-Naphthaldehyde ||  ||   ||
 * 3-hydroxybenzaldehyde ||  ||   ||
 * 3,4-dihydroxybenzaldehyde ||  ||   ||
 * 4-chlorobenzaldehyde ||  ||   ||
 * 2-hydroxy-3-methoxy benzaldehyde (o-vanillin) ||  ||   ||
 * Benzaldehyde ||  ||   ||
 * 3-methoxy benzaldehyde ||  ||   ||
 * Aniline ||  ||   ||
 * Methylamine ||  ||   ||
 * Furfurylamine ||  ||   ||
 * 5-Methyl furfurylamine ||  ||   ||
 * 2-Chloroaniline ||  ||   ||
 * Benzylamine ||  ||   ||
 * **[|173B14-4]** || [|InChI=1/C34H36N2O2/c1-22-12-14-27(15-13-22)32(33(38)35-34(2,3)4)3 ​6(5)29(37)11-7-8-23-16-17-26-19-18-24-9-6-10-25-20-21-28(23)31(26​ )30(24)25/h6,9-10,12-21,32H,7-8,11H2,1-5H3,(H,35,38] || [|KNHNINYGWDFMQZ]-[|UHFFFAOYAI] ||
 * **[|173G19-4]** || [|InChI=1/C30H32N2O4/c1-4-5-18-31-30(34)29(25-19-26(35-2)21-27(20-2 ​5)36-3)32(22-24-14-10-7-11-15-24)28(33)17-16-23-12-8-6-9-13-23/h6​ -15,19-21,29H,4-5,18,22H2,1-3H3,(H,31,34)] || [|VOGZWAORWZGOTE]-[|UHFFFAOYAY] ||
 * **[|173N26-4]** || [|InChI=1/C33H41ClN2O6S/c1-4-5-6-7-8-9-10-18-30(37)36(28-16-12-11-1 ​5-27(28)34)31(26-14-13-17-29(42-3)32(26)38)33(39)35-23-43(40,41)2​ 5-21-19-24(2)20-22-25/h11-17,19-22,31,38H,4-10,18,23H2,1-3H3,(H,3​5,39)] || [|KYIHNAOLRBXNCE]-[|UHFFFAOYAO] ||
 * [|173O27-4]** || [|InChI=1/C29H28N2O7S/c1-20-9-12-24(13-10-20)39(36,37)19-30-29(35)2 ​8(22-6-3-2-4-7-22)31(18-23-8-5-15-38-23)27(34)17-21-11-14-25(32)2​ 6(33)16-21/h2-16,28,32-33H,17-19H2,1H3,(H,30,35)] || [|UBEBESNSOHELHI]-[|UHFFFAOYAZ] ||