1,2-Dichloroethane → 4-(2,6-Difluoro-phenyl)-3-[1-[3-methyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1839829Notes

Reaction equation

HRID 1839829 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1/[C:11](=[CH:19]/[C:20]1[NH:24][CH:23]=[C:22]([C:25](O)=[O:26])[C:21]=1[CH3:28])/[C:12](=[O:18])[NH:13]2.[N:29]1([CH2:34][C@@H:35]2[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]2)[CH2:33][CH2:32][CH2:31][CH2:30]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1/[C:11](=[CH:19]/[C:20]1[NH:24][CH:23]=[C:22]([C:25]([N:37]3[CH2:38][CH2:39][CH2:40][C@@H:35]([CH2:34][N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)[CH2:36]3)=[O:26])[C:21]=1[CH3:28])/[C:12](=[O:18])[NH:13]2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 600614295-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 600614804-(2,6-Difluoro-phenyl)-3-[1-[3-methyl-4-((s)-3-pyrrolidin-1-ylmethyl-piperidine-1-carbonyl)-1h-pyrrol-2-yl]-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[4-(2,6-Difluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-4-methyl-1H-pyrrole-3-carboxylic acid (114 mg, 0.3 mmol) was coupled with (R)-3-pyrrolidin-1-ylmethyl-piperidine (99 mg, 2 eq.), HOBt (1 eq.), EDC (1.5 eq.) and TEA (3 drops) in THF (1 mL) and aceonitrile (1 mL) at rt for overnight to give 111.3 mg (70%) of the titled compound as a yellow solid.

Sources & evidence

ORD record
ord-3eb7c0213ba04101acd698d078df3122
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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