Water → HCID 118208669, compound

HRID 595302Notes

Reaction equation

HRID 595302 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][NH:13][CH:14]=2)[N:7]=[C:6]([NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=2)[CH:5]=1.Cl[CH2:27][C:28]1([CH2:31]C)[CH2:30][O:29]1.O>CN(C=O)C>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][N:13]([CH2:27][C:28]3([CH3:31])[CH2:30][O:29]3)[CH:14]=2)[N:7]=[C:6]([NH:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[CH:18][N:17]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 108443802-(Chloromethyl)-1,2-epoxybutaneHCID 72707043HCID 72707043, compound

Product 1

HCID 118208669HCID 118208669, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (20.7 mg, 0.52 mmol) was added to a solution of 4-methyl-6-(1H-pyrazol-4-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)pyridin-2-amine (150 mg, 0.47 mmol) in DMF (2 mL). The mixture was stirred for ten minutes after which time 2-(chloromethyl)-2-ethyloxirane (150 mg, 1.41 mmol) was added. The mixture was stirred at room temperature for 2 h, water was added, and the mixture was extracted with EtOAc. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford 4-methyl-6-(1-((2-methyloxiran-2-yl)methyl)-1H-pyrazol-4-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)pyridin-2-amine. MS ESI calc'd. for C19H19F3N5O [M+H]+ 390. found 390.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51edf845c0d445799f34be7fb26dac2a
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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