Cyclohexanecarboxaldehyde → HCID 57567656, compound

HRID 883699Notes

Reaction equation

HRID 883699 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([N:15]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])=[CH:12][C:7]=2[N:6]=[C:5]1[NH:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1.[CH:37]1([CH:43]=O)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[BH4-].C(OC1C=CC=CC=1C=O)C1C=CC=CC=1>CO.ClCCl>[CH:37]1([CH2:43][NH:1][CH2:2][CH2:3][N:4]2[C:8]3[CH:9]=[CH:10][C:11]([C:13]([N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:20][CH:21]([CH3:22])[CH3:23])=[O:14])=[CH:12][C:7]=3[N:6]=[C:5]2[NH:24][C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 28123BorohydrideHCID 3447842-(Benzyloxy)benzaldehydeHCID 69027345HCID 69027345, compound

Product 1

HCID 57567656HCID 57567656, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-aminoethyl)-N,N-diisobutyl-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-5-carboxamide (30 mg, 1 eq) and cyclohexanecarboxaldehyde (5 mg, 0.8 eq) in methanol (0.7 ml) is stirred at a temperature of approximately 20° C. for 4 hours. Borohydride resin (48 mg, 2.5 mmol/g, Amberlite®, IRA-400) is added and the mixture is stirred for 18 hours then dichloromethane (0.5 ml) and benzyloxybenzaldehyde Wang resin (37 mg, 3.22 mmol/g, Novabiochem) are added. After stirring overnight, the mixture is filtered and the filtrate is evaporated under reduced pressure in order to produce the expected compound in the form of a beige foam (18 mg, 65%).

Workup

  1. stirringAfter stirring overnight
  2. filtrationthe mixture is filtered
  3. customthe filtrate is evaporated under reduced pressure in order

Sources & evidence

ORD record
ord-51213cf7be74412eadea33b512803d40
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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