Potassium Carbonate → N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide

HRID 1159887Notes

Reaction equation

HRID 1159887 reaction equation
[OH-].[K+].[Cl:3][C:4]1[N:9]=[C:8]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:28])[C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])[CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=1.[I-].[NH2:30][N+:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:3][C:4]1[N:9]=[C:8]([C:10]2[C:11]([C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:28])[C:20]4[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=4[F:27])[CH:15]=[CH:16][CH:17]=3)=[N:30][N:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=23)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 59513791HCID 59513791, compound

Product 1

HCID 59513803N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamideYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOH (1.0 g, 17.4 mmol) was ground to a powder and added to a rt solution of N-{3-[(2-chloro-4-pyrimidinyl)ethynyl]phenyl}-2,6-difluorobenzamide (6.4 g, 17.4 mmol), 1-aminopyridinium iodide (3.85 g, 17.4 mmol), K2CO3 (4.8 g, 34.7 mmol) and DMSO (100 mL) at rt. The reaction was stirred for 3 h and the product crystallized out of the reaction mixture. The reaction was combined with an equal volume of water and the suspension was filtered. The solids were washed with water, then triturated with diethyl ether. The resulting brown solid was dried for 24 h at 60° C. under vacuum to give 7.1 g (89%) of the crude title compound as a brown powder. MS (ESI): M+H=461.99.

Workup

  1. customthe product crystallized out of the reaction mixture
  2. filtrationthe suspension was filtered
  3. washThe solids were washed with water
  4. customtriturated with diethyl ether
  5. customThe resulting brown solid was dried for 24 h at 60° C. under vacuum

Sources & evidence

ORD record
ord-de05e61e9cf3407dbdbef2bb4291ca89
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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