Trifluoroacetic acid → 1-cyclohexyl-2-(3-furyl)-N-[2-(4-hydroxyphenyl)-1-(2-pyridyl)ethyl]benzimidazole-5-carboxamide

HRID 1018257Notes

Reaction equation

HRID 1018257 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(=N)C1C=CC=CC=1.C(OC([O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=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.C(O)(C(F)(F)F)=O>>[OH:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH:2]([NH:1][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:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 195092-PyridinemethanamineHCID 428166PhenylmethanimineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 226691824-Tert-butoxycarbonyloxy-benzyl chloride

Product 1

HCID 4908561-cyclohexyl-2-(3-furyl)-N-[2-(4-hydroxyphenyl)-1-(2-pyridyl)ethyl]benzimidazole-5-carboxamide

Procedure

2-(Aminomethyl)pyridine was converted to its benzaldehyde imine (benzaldehyde in DCM with 4A molecular sieves) and alkylated with 4-tert-butoxycarbonyloxy-benzyl chloride following an adaptation of the procedure described by Y. Wang et al. (Synth. Commun. 1992, 22, 265). The resulting racemic amine was coupled to the carboxylic acid of example 2 under the usual conditions, and deprotected with TFA to give the title compound of example 38 after purification by preparative C18 reversed-phase HPLC.

Sources & evidence

ORD record
ord-8889f483dc0f4b26a4b2ffd472455761
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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