Réaction #169900

ord-2d1203d754da490684a27a1c8980cbde

Équation de réaction

CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
Nc1nsnc1C(=S)Nc1ccc(F)c(Br)c1
4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamide
COS(=O)(=O)C(F)(F)F
methyl trifluoromethanesulfonate
CSC(=Nc1ccc(F)c(Br)c1)c1nsnc1N
desired product
Rendement 98.0%
CSC(=Nc1ccc(F)c(Br)c1)c1nsnc1N
Methyl 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbimidothioate
Rendement 98.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagewashed with water (50 mL) and brine (50 mL)
  2. 2
    Séchagedried with sodium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    Concentrationconcentrated

Mode opératoire

A solution of 4-amino-N-(3-bromo-4-fluorophenyl)-1,2,5-thiadiazole-3-carbothioamide (130 mg, 0.4 mmol) in dichloromethane (5.2 mL) was treated with methyl trifluoromethanesulfonate (64 μL, 0.6 mmol) followed by N,N-diisopropylethylamine (102 μL, 0.6 mmol) and stirred for 1 h. The reaction mixture was diluted with dichloromethane (100 mL), washed with water (50 mL) and brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (133 mg, 98%). LCMS for C10H9BrFN4S2 (M+H)+: m/z=346.8, 348.8.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08846726B2uspto-grants-2014_09