Piperidine → HCID 66604407, compound

HRID 1359694Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16]3)(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=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]([CH:37]=O)[NH:33][C:32]=1[CH3:39])=[O:30])[CH3:24].N1CCCCC1>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])=[C:34](/[CH:37]=[C:16]2\[C:17](=[O:22])[NH:18][C:19]3[C:15]\2=[CH:14][C:13]([S:10]([CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:11])=[O:12])=[CH:21][CH:20]=3)[NH:33][C:32]=1[CH3:39])=[O:30])[CH3:41]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-(3-methoxy-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one (100 mg, 0.32 mmol) and 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (84 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 125 mg (69%) of 5-[5-(3-methoxy-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-a87c8f08624c49ff8b712363c0a4f8e2
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599902B2

Reaction notes

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