4-Amino-2,6-difluorobenzotrifluoride → 2-(1,1-difluoroethyl)-N-[3,5-difluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 591251Notes

Reaction equation

HRID 591251 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]([F:14])([F:13])[CH3:12])[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=1.[NH2:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([C:24]([F:27])([F:26])[F:25])=[C:19]([F:28])[CH:18]=1>C(O)C>[F:13][C:11]([C:9]1[N:10]=[C:6]2[N:5]=[C:4]([CH3:15])[CH:3]=[C:2]([NH:16][C:17]3[CH:18]=[C:19]([F:28])[C:20]([C:24]([F:27])([F:25])[F:26])=[C:21]([F:23])[CH:22]=3)[N:7]2[N:8]=1)([F:14])[CH3:12]

Participants

4

Reactant 2

HCID 7178284-Amino-2,6-difluorobenzotrifluorideHCID 533918697-Chloro-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513475452-(1,1-difluoroethyl)-N-[3,5-difluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Intermediate 3 (0.1 g, 0.43 mmol) and 4-amino-2,6-difluorobenzotrifluoride (FLUOROCHEM, 0.085 g, 0.43 mmol) in ethanol (7 mL) was stirred at room temperature overnight. Solvent was removed in vacuo and the residue was taken up in DCM. The resulting solution was washed with 1N Na2CO3, then with brine and dried over anhydrous Na2SO4 to yield a yellow oil which was purified by flash chromatography (Si, eluting with Hexane/EtOAc mixtures from 100:0 to 50:50%) to afford the title compound as a pale yellow solid.

Workup

  1. customSolvent was removed in vacuo
  2. washThe resulting solution was washed with 1N Na2CO3
  3. dry with materialwith brine and dried over anhydrous Na2SO4
  4. customto yield a yellow oil which
  5. customwas purified by flash chromatography (Si, eluting with Hexane/EtOAc mixtures from 100:0 to 50:50%)

Sources & evidence

ORD record
ord-d551a552038945c9b137d26d791ed796
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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