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

HRID 1359811Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([NH:33][CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][N:39]([C:42](=[O:48])[CH2:43][O:44]C(=O)C)[CH2:38][CH2:37]2)=[O:32])[C:25]=1[CH3:49])(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([NH:33][CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][N:39]([C:42](=[O:48])[CH2:43][OH:44])[CH2:38][CH2:37]2)=[O:32])[C:25]=1[CH3:49])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of acetic acid 2-{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]-piperazin-1-yl}-2-oxo-ethyl ester (100 mg), 10% potassium carbonate in water and methanol (5 mL) was stirred at 40° C. for overnight. The reaction was concentrated, extracted with DCM. The combined DCM was dried, concentrated and purified on a silica gel column to give the titled compound as an orange-red solid. MS m/z 686 [M−1].

Workup

concentrationThe reaction was concentrated
extractionextracted with DCM
dry with materialThe combined DCM was dried
concentrationconcentrated
custompurified on a silica gel column

Sources & evidence

ORD record: ord-41f32135918e4963b8bd2ad15106ef36
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599902B2

Reaction notes

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