1,1-Dicyclohexyl-3-(4-bromomethyl-thiazol-2-yl)urea → 2-[2-(3,3-Dicyclohexylureido)-thiazol-4-ylmethyl-sulfanyl)-1H-imidazole-4-carboxylic acid ethyl ester

HRID 1818372Notes

Reaction equation

HRID 1818372 reaction equation
[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[C:14]([CH2:16]Br)[N:15]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([O:26][C:27]([C:29]1[N:30]=[C:31]([SH:34])[NH:32][CH:33]=1)=[O:28])[CH3:25]>>[CH2:24]([O:26][C:27]([C:29]1[N:30]=[C:31]([S:34][CH2:16][C:14]2[N:15]=[C:11]([NH:10][C:8]([N:7]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:9])[S:12][CH:13]=2)[NH:32][CH:33]=1)=[O:28])[CH3:25].[CH:1]1([N:7]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:9])[NH:10][C:11]2[S:12][CH:13]=[C:14]([CH2:16][S:34][C:31]3[NH:32][CH:33]=[C:29]([C:27]([OH:28])=[O:26])[N:30]=3)[N:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 866111831,1-Dicyclohexyl-3-(4-bromomethyl-thiazol-2-yl)ureaHCID 178469909HCID 178469909, compound

Product 2

HCID 1784699062-[2-(3,3-Dicyclohexylureido)-thiazol-4-ylmethyl-sulfanyl)-1H-imidazole-4-carboxylic acid ethyl esterYield 20%HCID 178524801HCID 178524801, compound

Procedure

2-[2-(3,3-Dicyclohexylureido)-thiazol-4-ylmethylsulfanyl)-1H-imidazole-4-carboxylic acid ethyl ester was prepared in 20% yield as described in general procedure L from 1,1-dicyclohexyl-3-(4-bromomethyl-thiazol-2-yl)urea and 2-mercapto-1H-imidazole-4-carboxylic acid ethyl ester. The ester (30 mg, 0.06 mmol) was hydrolysed using general procedure F to give 2-[2-(3,3-dicyclohexylureido)-thiazol-4-ylmethylsulfanyl)-1H-imidazole-4-carboxylic acid in 80% yield (22 mg).

Sources & evidence

ORD record
ord-cb46f039e3bb402b8b1e917a89c179cd
Source dataset
uspto-grants-2009_10
Patent number
US07598391B2

Reaction notes

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