2-(3,3-Dicyclohexylureido)-thiazole-4-carboxylic acid → 3-{[2-(3,3-Dicyclohexylureido)-thiazole-5-carbonyl]-amino}-benzoic acid

HRID 253881Notes

Reaction equation

HRID 253881 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([C:13]2[S:17][C:16]([NH:18][C:19]([N:21]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:20])=[N:15][CH:14]=2)=[O:12])[CH:5]=1.C1(N(C2CCCCC2)C(=O)NC2SC=C(C(O)=O)N=2)CCCCC1>>[CH:28]1([N:21]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:19](=[O:20])[NH:18][C:16]2[S:17][C:13]([C:11]([NH:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:34])=[O:2])=[O:12])=[CH:14][N:15]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 578836042-(3,3-Dicyclohexylureido)-thiazole-4-carboxylic acidHCID 578839283-{[2-(3,3-Dicyclohexylureido)-thiazole-5-carbonyl]-amino}-benzoic acid methyl ester

Product 1

HCID 578838163-{[2-(3,3-Dicyclohexylureido)-thiazole-5-carbonyl]-amino}-benzoic acidYield 40%

Procedure

3-{[2-(3,3-Dicyclohexylureido)-thiazole-5-carbonyl]-amino}-benzoic acid was prepared in 40% yield as described in general procedure F from 3-{[2-(3,3-Dicyclohexylureido)-thiazole-5-carbonyl]-amino}-benzoic acid methyl ester, which in turn was prepared in 21% yield as described in general procedure H using 2-(3,3-dicyclohexylureido)-thiazole-4-carboxylic acid and methyl-3-amino benzoate.

Workup

  1. customwas prepared in 21% yield

Sources & evidence

ORD record
ord-95b06cdd958e4254af72e397858d66b8
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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