Cyclopentanone → 2-[(R)-2-(7-cyclopentylamino-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid

HRID 2089618Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH2:4][C@@H:5]1[CH2:9][S:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([N+:19]([O-])=O)[CH:18]=2)[NH:15][C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:13]3)=[N:6]1.[C:29]1(=O)[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([NH:19][C:17]2[CH:18]=[C:10]([C:7]3[S:8][CH2:9][C@@H:5]([CH2:4][C:3]([OH:2])=[O:28])[N:6]=3)[CH:11]=[C:12]3[C:16]=2[NH:15][C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:13]3)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

Reactant 2

HCID 8452Cyclopentanone

HCID 684764212-[(R)-2-(7-nitro-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester

Product 1

HCID 684757932-[(R)-2-(7-cyclopentylamino-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid

Procedure

2-[(R)-2-(7-nitro-2-phenyl-1H-indol-5-yl)-4,5-dihydro-thiazol-4-yl]-acetic acid methyl ester prepared in Step B and cyclopentanone were reacted according to the same procedures as Examples 1 and 30 to give the title compound.

Sources & evidence

ORD record: ord-ab87f0ec1cd348a0bc2aa98fc1ed56d9
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436038B2

Reaction notes

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