Piperidine → HCID 66604206, compound

HRID 1359692Notes

Reaction equation

[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11]([CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17]#[N:18])(=[O:13])=[O:12])[CH:8]=2)[NH:3]1.[CH2:23]([N:25]([CH2:40][CH3:41])[CH2:26][CH2:27][NH:28][C:29]([C:31]1[C:35]([CH3:36])=[C:34](C=O)[NH:33][C:32]=1[CH3:39])=[O:30])[CH3:24].N1CCCC[CH2:43]1>C(O)C>[CH2:40]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][NH:28][C:29]([C:31]1[C:35]([CH3:36])=[CH:34][N:33](/[CH:43]=[C:10]2\[C:2](=[O:1])[NH:3][C:4]3[C:9]\2=[CH:8][C:7]([S:11]([CH2:14][C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])(=[O:12])=[O:13])=[CH:6][CH:5]=3)[C:32]=1[CH3:39])=[O:30])[CH3:41]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-(2-Oxo-2,3-dihydro-1H-indole-5-sulfonylmethyl)-benzonitrile (100 mg, 0.32 mmol) and 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (85 mg, 0.32 mmol) in ethanol (4 mL) was added piperidine (0.1 mL). The reaction mixture was stirred at 25° C. for three days. The solvent was evaporated and the residue was purified on a silica gel column eluting with MeOH—CH2Cl2 1:9 to provide 116 mg (65%) of [5-(2-Cyano-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide as a pale orange solid.

Workup

customThe solvent was evaporated
customthe residue was purified on a silica gel column
washeluting with MeOH—CH2Cl2 1:9

Sources & evidence

ORD record: ord-77353fde17ed4c36a58dba97b6211a51
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599902B2

Reaction notes

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