HCID 86712745, compound → HCID 86712744, compound

HRID 1779119Notes

Reaction equation

HRID 1779119 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([C:17]#[C:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][C:26]([NH2:28])=[O:27])[C:14]([C:29]([F:32])([F:31])[F:30])=[CH:13][N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>CN(C=O)C.CCO.CCN(CC)CC.[Pd]>[C:1]([C:4]1[N:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][C:26]([NH2:28])=[O:27])[C:14]([C:29]([F:30])([F:31])[F:32])=[CH:13][N:12]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 1

HCID 86712745HCID 86712745, compound

Product 1

HCID 86712744HCID 86712744, compoundYield 57.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 2-(2-((2-((6-acetylpyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)acetamide (A142) (0.347 g, 0.790 mmol) in DMF (20 mL), EtOH (3 mL) and Et3N (1 mL) containing 10% palladium on carbon (0.110 g) was stirred under a hydrogen atmosphere for 20 hours. The reaction mixture was filtered through a pad of Celite and the solvent was concentrated in vacuo. The crude material was adsorbed onto silica gel and purified by silica gel column chromatography (CombiFlash Rf, 24 g SiO2 Cartridge, 0-10% MeOH in DCM) to give the title compound (A143) as a white solid (0.200 g, 57%). LCMS-B: 6.80 min; m/z 444 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe solvent was concentrated in vacuo
  3. custompurified by silica gel column chromatography (CombiFlash Rf, 24 g SiO2 Cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-56663aac1d6e4fd6bee318e9645d911b
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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