4-Aminophenylsulphur pentafluoride → 2-cyclopropyl-5-methyl-N-[4-(pentafluoro-lambda6-sulfanyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

HRID 591247Notes

Reaction equation

HRID 591247 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=[C:6]2[N:5]=[C:4]([CH3:14])[CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([F:27])([F:26])([F:25])([F:24])[F:23])=[CH:18][CH:17]=1>C(O)C>[CH:11]1([C:9]2[N:10]=[C:6]3[N:5]=[C:4]([CH3:14])[CH:3]=[C:2]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([S:22]([F:27])([F:23])([F:24])([F:25])[F:26])=[CH:18][CH:17]=4)[N:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 27791904-Aminophenylsulphur pentafluorideHCID 533918677-Chloro-2-cyclopropyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine

Product 1

HCID 513475462-cyclopropyl-5-methyl-N-[4-(pentafluoro-lambda6-sulfanyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of Intermediate 20 (0.04 g, 0.192 mmol) in ethanol (2.5 mL), 4-aminophenylsulfur pentafluoride (MANCHESTER, 0.042 g, 0.192 mmol) was added and the mixture was stirred under reflux overnight. Solvent was removed in vacuo and the crude mixture was purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 10 to 100%) to yield the title compound as a beige solid.

Workup

  1. additionwas added
  2. temperatureunder reflux overnight
  3. customSolvent was removed in vacuo
  4. customthe crude mixture was purified by preparative HPLC (SunFire 19×150 mm, H2O 0.1% TFA-ACN 0.1% TFA gradient from 10 to 100%)

Sources & evidence

ORD record
ord-a1603277a1ae49b2b9f61a4b92f3a6fc
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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