Benzaldehyde → HCID 70275516, compound

HRID 399122Notes

Reaction equation

HRID 399122 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) δ7.62 (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-eab82443616a4324a6a8fe240298de49
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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