Benzylamine → Racemic 1-cyclohexyl-2-furan-3-yl-1H-benzimidazole-5-carboxylic acid [2-(4-hydroxy-phenyl)-1-phenyl-ethyl]-amide

HRID 1007698Notes

Reaction equation

HRID 1007698 reaction equation
[CH:1](=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9](N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O:21]C(OC(Cl)C1C=CC=CC=1)=O)(C)(C)C.[CH:33]1([N:39]2[C:43]3[CH:44]=[CH:45][C:46]([C:48](O)=[O:49])=[CH:47][C:42]=3[N:41]=[C:40]2[C:51]2[CH:55]=[CH:54][O:53][CH:52]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C1COCC1>[OH:21][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH:1]([NH:8][C:48]([C:46]2[CH:45]=[CH:44][C:43]3[N:39]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[C:40]([C:51]4[CH:55]=[CH:54][O:53][CH:52]=4)=[N:41][C:42]=3[CH:47]=2)=[O:49])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 428166PhenylmethanimineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 67113782Tert-butoxycarbonyloxy-benzyl chloride

Product 1

HCID 23378163Racemic 1-cyclohexyl-2-furan-3-yl-1H-benzimidazole-5-carboxylic acid [2-(4-hydroxy-phenyl)-1-phenyl-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general method of example 37, the benzaldehyde imine of benzylamine was alkylated with tert-butoxycarbonyloxy-benzyl chloride using lithium hexamethyldisilizane as a base at low temperature (−78° C.) in THF as solvent. Following the usual work up, the racemic amine was coupled to the carboxylic acid of example 2, to give after removal of the Boc group and purification by preparative C18 reversed-phase HPLC, the title compound of example 39.

Workup

  1. customto give
  2. customafter removal of the Boc group and purification by preparative C18 reversed-phase HPLC

Sources & evidence

ORD record
ord-f603a3f303404afe8d7851f2ef962baf
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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