3,4-Difluorobenzene-1-sulfonyl chloride → 3,4-Difluoro-N-[2-methyl-6-((2S,3'S)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 536315Notes

Reaction equation

HRID 536315 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1.[F:20][C:21]1[CH:22]=[C:23]([S:28](Cl)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[F:27]>ClCCl.N1C=CC=CC=1>[F:20][C:21]1[CH:22]=[C:23]([S:28]([NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([N:9]3[CH2:13][CH2:12][C@H:11]([N:14]4[CH2:18][CH2:17][CH2:16][C@@H:15]4[CH3:19])[CH2:10]3)=[CH:5][CH:6]=2)(=[O:29])=[O:30])[CH:24]=[CH:25][C:26]=1[F:27]

Participants

5

Reactant 2

HCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 674803792-Methyl-6-((2S,3'S)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl-amine

Product 1

HCID 545970823,4-Difluoro-N-[2-methyl-6-((2S,3'S)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-benzenesulfonamideYield 36%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized substantially in the same manner as Example 3 by coupling of 2-methyl-6-((2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-ylamine (0.025 g, 0.096 mmol) with 3,4-difluorobenzenesulfonyl chloride (0.061 g, 0.288 mmol) in dichloromethane (3 mL) and pyridine (0.5 mL) to obtain 0.015 g (36%) of the title compound.

Sources & evidence

ORD record
ord-08eabc377aea450e87a0c88d3b4ec7f2
Source dataset
uspto-grants-2014_10
Patent number
US08859588B2

Reaction notes

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