4-(Trifluoromethyl)aniline → 2-(1,1-difluoropropyl)-5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 591252Notes

Reaction equation

HRID 591252 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:15])([F:14])[CH2:12][CH3:13])[N:10]=[C:6]2[N:5]=[C:4]([CH3:16])[CH:3]=1.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(O)C>[F:14][C:11]([C:9]1[N:10]=[C:6]2[N:5]=[C:4]([CH3:16])[CH:3]=[C:2]([NH:23][C:22]3[CH:24]=[CH:25][C:19]([C:18]([F:17])([F:26])[F:27])=[CH:20][CH:21]=3)[N:7]2[N:8]=1)([F:15])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 533919807-Chloro-2-(1,1-difluoropropyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513475422-(1,1-difluoropropyl)-5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of Intermediate 7 (0.1 g, 0.405 mmol) and 4-(trifluoromethyl)aniline (ALDRICH, 0.051 mL, 0.405 mmol) in ethanol (5 mL) was heated at 50° C. for 1 h. The reaction mixture was concentrated under vacuum, redissolved in DCM (20 mL) and washed with aq. Na2CO3 (2×15 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under vacuum to afford a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionredissolved in DCM (20 mL)
  3. washwashed with aq. Na2CO3 (2×15 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto afford a white solid

Sources & evidence

ORD record
ord-1d6cf148cb0142baa370c9079d677459
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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