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

HRID 1359827Notes

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]([C:30]([NH:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][N:38]([C:41](=[O:47])[CH2:42][O:43]C(=O)C)[CH2:37][CH2:36]2)=[O:31])[C:25]=1[CH3:48])(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>O.CO>[OH:43][CH2:42][C:41]([N:38]1[CH2:39][CH2:40][N:35]([CH2:34][CH2:33][NH:32][C:30]([C:26]2[C:25]([CH3:48])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])(=[O:12])=[O:11])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:31])[CH2:36][CH2:37]1)=[O:47]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of acetic acid 2-{4-[2-({5-[5-(2,6-dichlorophenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-ethyl]-piperazin-1-yl}-2-oxo-ethyl ester (from the above reaction) and 10% potassium carbonate (2.67 g) in water (20 mL) and methanol (10 mL) was stirred at 40° C. for overnight. The precipitate was collected by vacuum filtration, washed with methanol, water and dried to give 305 mg (45% for 4 steps) of the titled compound as a yellow solid.

Workup

filtrationThe precipitate was collected by vacuum filtration
washwashed with methanol, water
customdried

Sources & evidence

ORD record: ord-4bfa43908b7044b99c140ba596f21f78
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599902B2

Reaction notes

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