4-Thiazoleacetic acid, 2-amino-, ethyl ester → (2-{[1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester

HRID 1715849Notes

Reaction equation

HRID 1715849 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].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[S:22]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([C:35](O)=[O:36])[CH:33]=2)[CH2:28][CH2:27][CH2:26]1)(=[O:24])=[O:23]>>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:35]([C:32]2[CH:33]=[C:34]3[C:29]([CH2:28][CH2:27][CH2:26][N:25]3[S:22]([C:16]3[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=3[O:14][CH3:13])(=[O:24])=[O:23])=[CH:30][CH:31]=2)=[O:36])[S:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 684338071-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid

Product 1

HCID 86761181(2-{[1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester

Procedure

1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-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-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid and yielded (2-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-thiazol-4-yl)-acetic acid ethyl ester, which was hydrolyzed to (2-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-thiazol-4-yl)-acetic acid in step 4, MS (ISP): m/e=502.0 (M+H).

Sources & evidence

ORD record
ord-30b44aa473ee4989a469ddfa56187420
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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