HCID 86712345, compound → 1-(2-(2-(2-((1-Methyl-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592483Notes

Reaction equation

HRID 592483 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]3)[C:11]([C:28]([F:31])([F:30])[F:29])=[CH:10][N:9]=2)[CH:4]=[N:3]1>CN(C=O)C.CCOC(C)=O.CCN(CC)CC.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3([C:25]([NH2:27])=[O:26])[CH2:24][CH2:23]3)[C:11]([C:28]([F:29])([F:31])[F:30])=[CH:10][N:9]=2)[CH:4]=[N:3]1

Participants

6

Reactant 1

HCID 86712345HCID 86712345, compound

Product 1

HCID 732954671-(2-(2-(2-((1-Methyl-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamideYield 74%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-((2-((1-methyl-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethynyl)phenyl)cyclopropanecarboxamide A75 (0.120 g, 0.281 mmol) and 10% Pd/C (0.135 g) in DMF (3 mL), EtOAc (5 mL) and Et3N (0.5 mL) was stirred under a hydrogen atmosphere for 16 hours. The mixture was filtered through Celite and concentrated under reduced pressure before purification by silica gel column chromatography (0-15% MeOH in EtOAc). The product was triturated with Et2O and the resulting precipitate was collected to give the title compound 65 (0.090 g, 74%). LCMS-D: rt 3.316 min; m/z 431.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure before purification by silica gel column chromatography (0-15% MeOH in EtOAc)
  3. customThe product was triturated with Et2O
  4. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-f593faf02fe846d7b7e09c0f7a3cd65c
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

Loading…