Benzaldehyde → HCID 70275516, compound

HRID 365448Notes

Reaction equation

HRID 365448 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][C@@H:9]([NH:11][C:12](=[O:28])[CH2:13][C:14]2[N:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)[CH:17]=[N:16][CH:15]=2)[CH2:8][NH:7][CH2:6]1)=[O:4].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:37]([BH3-])#N.[Na+]>CO>[CH2:37]([N:7]1[CH2:8][C@H:9]([NH:11][C:12](=[O:28])[CH2:13][C:14]2[N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=3)[CH:17]=[N:16][CH:15]=2)[CH2:10][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6]1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 70273938HCID 70273938, compound

Product 1

HCID 70275516HCID 70275516, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cis-3-Methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-yl)acetylamino]piperidine (35.3 mg, 0.093 mmol), benzaldehyde (32.5 uL, 0.278 mmol), and sodium cyanoborohydride (17.5 mg, 0.278 mmol) was dissolved in MeOH (2 mL) and stirred overnight at ambient temperature. The solution was concentrated under reduced pressure and chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH) to give the title compound. 1H NMR (CDCl3) δ 7.62 (d, 2H, J=8 Hz), 7.52 (s, 1H), 7.11-7.31 (m, 7H), 6.99 (s, 1H), 6.25 (br s, 1H), 5.24 (s, 2H), 3.86-3.96 (m, 1H), 3.65 (s, 3H), 3.29 (s, 2H), 2.48-2.83 (m, 8H), 2.13-2.24 (m, 1H), 1.83-1.95 (m, 1H), 1.50-1.65 (m, 1H). FAB MS 486 (M+1)

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customchromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH)

Sources & evidence

ORD record
ord-3e84b9900e5d49dcaa96f1539c16a8bf
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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