Trifluoroacetic acid → 2-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-piperazin-1-yl-ethyl)-acetamide

HRID 1359809Notes

Reaction equation

HRID 1359809 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17](=[O:49])[CH2:18][C:19]2[C:23]([CH3:24])=[C:22](/[CH:25]=[C:26]3\[C:27](=[O:47])[NH:28][C:29]4[C:34]\3=[CH:33][C:32]([S:35]([CH2:38][C:39]3[C:44]([Cl:45])=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:46])(=[O:37])=[O:36])=[CH:31][CH:30]=4)[NH:21][C:20]=2[CH3:48])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:45][C:44]1[CH:43]=[CH:42][CH:41]=[C:40]([Cl:46])[C:39]=1[CH2:38][S:35]([C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27](=[O:47])/[C:26]/2=[CH:25]\[C:22]1[NH:21][C:20]([CH3:48])=[C:19]([CH2:18][C:17]([NH:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:49])[C:23]=1[CH3:24])(=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 699942334-[2-(2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3 Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 590775552-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-piperazin-1-yl-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[2-(2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (from the above reaction) and TFA (1 mL) in DCM (10 mL) was stirred at rt for overnight. The reaction was concentrated and purified to give 590 mg of the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-635a4d7a711142bc8123c9ffe800fb8b
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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