1-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride → N-(3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzyl)-1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1625487Notes

Reaction equation

HRID 1625487 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH2:17][NH2:18])[CH:14]=[CH:15][CH:16]=3)[C:3]=12.[F:28][C:29]1[CH:30]=[C:31]([CH:43]=[CH:44][C:45]=1[F:46])[CH2:32][N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39](Cl)=[O:40])[C:34]1=[O:42]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=3)[CH2:17][NH:18][C:39]([C:35]3[C:34](=[O:42])[N:33]([CH2:32][C:31]4[CH:43]=[CH:44][C:45]([F:46])=[C:29]([F:28])[CH:30]=4)[CH:38]=[CH:37][CH:36]=3)=[O:40])[C:3]=12

Participants

4

Reactant 2

HCID 593623351-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chlorideHCID 59362394(3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanamine

Product 1

HCID 68609885N-(3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzyl)-1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

43 mg of (3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)methanamine, 32 mg of crude 1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carbonyl chloride were dissolved in DCM, TEA was added, then the resulted mixture was stirred at room temperature for overnight. The solvent was removed on a rotary evaporator and the crude was purified by chromatography to give 32 mg of N-(3-(4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzyl)-1-(3,4-difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxamide, yield: 50%.

Workup

  1. additionTEA was added
  2. customThe solvent was removed on a rotary evaporator
  3. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-5823c1c95459401e87f46913eaf3dc21
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

Loading…