5-(2,6-Difluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one → 3-[1-[4-((s)-2-Cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1h-pyrrol-2-yl]-meth-(z)-ylidene]-5-(2,6-difluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one

HRID 1359767Notes

Reaction equation

HRID 1359767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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])[CH2:16]2)(=[O:12])=[O:11].[CH:23]1([NH:26][CH2:27][C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2[C:33]([C:35]2[C:36]([CH3:43])=[C:37]([CH:41]=O)[NH:38][C:39]=2[CH3:40])=[O:34])[CH2:25][CH2:24]1>N1CCCCC1.C(O)C>[CH:23]1([NH:26][CH2:27][C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2[C:33]([C:35]2[C:36]([CH3:43])=[C:37](/[CH:41]=[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]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])(=[O:12])=[O:11])=[CH:21][CH:20]=4)[NH:38][C:39]=2[CH3:40])=[O:34])[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 181799315-(2,6-Difluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-oneHCID 865886154-((S)-2-cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 590777583-[1-[4-((s)-2-Cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1h-pyrrol-2-yl]-meth-(z)-ylidene]-5-(2,6-difluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(2,6-difluoro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one (280 mg, 0.87 mmol), 4-((S)-2-cyclopropylaminomethyl-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (250 mg, 0.86 mmol) and piperidine (2 drops) in ethanol (2 mL) was stirred at rt for 4 days. The reaction was concentrated and purified on a silica gel column to give the titled compound.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-85377515695449c09b1221ba117aaa9c
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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