4-Chloro-2-methylbenzoic acid → HCID 491059, compound

HRID 1018297Notes

Reaction equation

HRID 1018297 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:6][C:5]=1[CH3:20].ClC1C=[CH:30][C:26]([C:27](O)=[O:28])=[C:25](C)[CH:24]=1.Cl.C[O:35][C:36](=[O:50])[C@H:37]([CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([OH:49])[CH:47]=2)[NH:42][CH:41]=1)[NH2:38]>>[CH:14]1([N:13]2[C:7]3[CH:6]=[C:5]([CH3:20])[C:4]([C:3]([OH:2])=[O:21])=[CH:9][C:8]=3[N:10]=[C:30]2[C:26]2[CH:25]=[CH:24][O:28][CH:27]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH:14]1([N:13]2[C:7]3[CH:6]=[C:5]([CH3:20])[C:4]([C:3]([NH:38][C@@H:37]([CH2:39][C:40]4[C:48]5[C:43](=[CH:44][CH:45]=[C:46]([OH:49])[CH:47]=5)[NH:42][CH:41]=4)[C:36]([OH:35])=[O:50])=[O:21])=[CH:9][C:8]=3[N:10]=[C:30]2[C:26]2[CH:25]=[CH:24][O:28][CH:27]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 3482694-Chloro-2-methylbenzoic acidHCID 23378470HCID 23378470, compoundHCID 24802218methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride

Product 2

HCID 491059HCID 491059, compoundHCID 3012619HCID 3012619, compound

Procedure

1-Cyclohexyl-2-furan-3-yl-6-methyl-1H-benzimidazole-5-carboxylic acid was prepared from 4-cyclohexylamino-2-methyl-5-nitrobenzoic acid methyl ester (Example 151) as described for the 4-methyl derivative (Example 151). The acid was coupled to 5-hydroxy-(S)-tryptophan methyl ester hydrochloride in the usual manner and following saponification of the methyl ester and purification by preparative C18 reversed-phase HPLC, the title compound of example 154 was obtained.

Workup

  1. customsaponification of the methyl ester and purification by preparative C18 reversed-phase HPLC

Sources & evidence

ORD record
ord-76560f347bbc456383d8145d6f78aff0
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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