p-Aminophenylacetic acid ethyl ester → HCID 68434771, compound

HRID 1715840Notes

Reaction equation

HRID 1715840 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([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:7]=1.[CH2:25]([O:27][C:28](=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1)[CH3:26]>>[CH2:25]([O:27][C:28](=[O:37])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([NH:36][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][N:11]3[S:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:23][CH3:24])(=[O:9])=[O:10])=[CH:15][CH:16]=2)=[O:21])=[CH:34][CH:35]=1)[CH3:26]

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 68432545HCID 68432545, compound

Product 1

HCID 68434771HCID 68434771, compound

Procedure

The title compound was prepared as for example 8, steps 1 to 4. Step 1 was performed using 5-chloro-2-methoxybenzensulfonyl chloride and yielded 1-(5-chloro-2-methoxybenzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester, which was hydrolyzed to 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid in step 2 and coupled to (4-amino-phenyl)-acetic acid ethyl ester and yielded (4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid ethyl ester, which was hydrolyzed to (4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-phenyl)-acetic acid in step 4, MS (ISP): m/e=499.1 (M−H).

Sources & evidence

ORD record
ord-5d6efd2a28684890973e1c5859315c28
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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