Piperidine → HCID 10188964, compound

HRID 1359693Notes

Reaction equation

[F:1][C:2]([F:24])([F:23])[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.[CH2:25]([N:27]([CH2:42][CH3:43])[CH2:28][CH2:29][NH:30][C:31]([C:33]1[C:37]([CH3:38])=[C:36]([CH:39]=O)[NH:35][C:34]=1[CH3:41])=[O:32])[CH3:26].N1CCCCC1>C(O)C>[CH2:42]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][NH:30][C:31]([C:33]1[C:37]([CH3:38])=[C:36](/[CH:39]=[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]([C:2]([F:1])([F:23])[F:24])[CH:4]=2)(=[O:12])=[O:11])=[CH:21][CH:20]=3)[NH:35][C:34]=1[CH3:41])=[O:32])[CH3:43]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-(3-Trifluoromethyl-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one (100 mg, 0.28 mmol) and 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide (75 mg, 0.28 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 105 mg (62%) of 2,4-dimethyl-5-[2-oxo-5-(3-trifluoromethyl-phenylmethanesulfonyl)-1,2-dihydro-indol-(3Z)-ylidenemethyl]-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-6c5a4d327313429d85b5ed9ec35b59de
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599902B2

Reaction notes

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