(1S,2S)-cyclopentane-1,2-dicarboxylic acid → (1S,2S)-2-(4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid

HRID 1645365Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[NH:24][C:25]4[C:30]([C:31]=3[CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=4[O:33][CH3:34])=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C@H:35]1([C:43]([OH:45])=[O:44])[CH2:39][CH2:38][CH2:37][C@@H:36]1[C:40]([OH:42])=O>>[CH3:34][O:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[NH:24][C:23]([C:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:40]([C@H:36]4[CH2:37][CH2:38][CH2:39][C@@H:35]4[C:43]([OH:45])=[O:44])=[O:42])[CH2:13][CH2:12]3)=[CH:19][CH:18]=1)=[O:22])=[C:31]2[CH3:32]

Participants

Reactant 2

HCID 727376(1S,2S)-cyclopentane-1,2-dicarboxylic acid

HCID 593651564-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59365164(1S,2S)-2-(4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid

Procedure

With a procedure similar to example above, (1S,2S)-2-(4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid was prepared from 4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester and (1S,2S)-cyclopentane-1,2-dicarboxylic acid. LCMS calcd for C28H32N4O5 (m/e) 504, obsd 505 (M+H).

Sources & evidence

ORD record: ord-49062983296140259adba91fa5a37f39
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124766B2

Reaction notes

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