4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 86621009, compound

HRID 1715839Notes

Reaction equation

HRID 1715839 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:23]([O:25][C:26](=[O:34])[CH2:27][C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[CH3:24]>>[CH2:23]([O:25][C:26](=[O:34])[CH2:27][C:28]1[N:29]=[C:30]([NH:33][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][N:11]3[S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:9])=[CH:15][CH:16]=2)=[O:21])[S:31][CH:32]=1)[CH3:24]

Participants

3

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 68435695HCID 68435695, compound

Product 1

HCID 86621009HCID 86621009, compound

Procedure

The title compound was prepared as for example 8, steps 1 to 4. Step 1 was performed using 3-chlorobenzensulfonyl chloride and yielded 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester) which was hydrolyzed to 1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid in step 2 and coupled to (2-amino-thiazol-4-yl)-acetic acid ethyl ester in step 3 to yield (2-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester. This was hydrolyzed to (2-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-thiazol-4-yl)-acetic acid in step 4: white solid, 0.08 g (96%), MS (ISP): m/e=476.0 (M−H).

Sources & evidence

ORD record
ord-646868f0053746ec9f37d5668a51cf17
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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