4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 86621010, compound

HRID 1715841Notes

Reaction equation

HRID 1715841 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)[CH3:2].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:37][CH3:38])=[C:18]([S:20]([N:23]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]3[CH:30]=[CH:31][C:32]([C:34](O)=[O:35])=[CH:33][C:24]2=3)(=[O:22])=[O:21])[CH:19]=1>>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:34]([C:32]2[CH:31]=[CH:30][C:25]3[CH2:26][CH2:27][CH2:28][CH2:29][N:23]([S:20]([C:18]4[CH:19]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]=4[O:37][CH3:38])(=[O:21])=[O:22])[C:24]=3[CH:33]=2)=[O:35])[S:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 68433680HCID 68433680, compound

Product 1

HCID 86621010HCID 86621010, compound

Procedure

1-(5-Chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-8-carboxylic acid was converted to the title compound in analogy to example 8, steps 3 and 4. Step 3 was performed using (2-amino-thiazol-4-yl)-acetic acid ethyl ester and 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-8-carboxylic acid and yielded (2-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-8-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester, which was hydrolyzed to (2-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-8-carbonyl]-amino}-thiazol-4-yl)-acetic acid in step 4, MS (ISP): m/e=536.1 (M+H).

Sources & evidence

ORD record
ord-2eb3149750204660be8986384d362376
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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