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

HRID 532007Notes

Reaction equation

HRID 532007 reaction equation
C(O)(=O)C1C=CC=CC=1.C[O:11][C:12](=[O:43])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([C:22]2[S:26][C:25]([NH:27][C:28]([N:30]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:29])=[N:24][CH:23]=2)=[O:21])[CH:14]=1.C1(N(C2CCCCC2)C(=O)NC2SC=C(C(O)=O)N=2)CCCCC1>>[CH:37]1([N:30]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:28](=[O:29])[NH:27][C:25]2[S:26][C:22]([C:20]([NH:19][C:15]3[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=3)[C:12]([OH:43])=[O:11])=[O:21])=[CH:23][N:24]=2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 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-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 40% yield
  2. customwas prepared in 21% yield

Sources & evidence

ORD record
ord-733829397727444a8f23f08fe84c76ce
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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