Réaction #163069

Équation de réaction

(S)-5,6-difluoro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amine

5-cyclopropyl-1H-pyrazol-3-amine

DIEA

→

title compound

Rendement 66.2%

(S)—N2-(5-Cyclopropyl-1H-pyrazol-3-yl)-3-fluoro-N6-(1-(4-fluorophenyl)ethyl)-5-nitropyridine-2,6-diamine

Rendement 66.2%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurecooled to room temperature
2. 2
   Autrequenched with water
3. 3
   ExtractionThe reaction was then extracted with DCM (2×75 ml)
4. 4
   Séchagethe combined organic fractions were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Mode opératoire

To a solution of (S)-5,6-difluoro-N-(1-(4-fluorophenyl)ethyl)-3-nitropyridin-2-amine (Method 23, 0.60 g, 2.0 mmol) in THF (10 ml) at room temperature was added 5-cyclopropyl-1H-pyrazol-3-amine (0.50 g, 4.0 mmol), and DIEA (0.26 g, 2.0 mmol). The reaction was then heated to 55° C. for 24 hours, cooled to room temperature, and quenched with water. The reaction was then extracted with DCM (2×75 ml), and the combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.53 g, 66%). 1H NMR (400 MHz, CD3OD) δ 8.00 (d, J=11.1 Hz, 1H), 7.38-7.35 (m, 2H), 7.07-7.02 (m, 2H), 6.17 (s, 1H), 5.41-5.39 (m, 1H), 1.93-1.87 (m, 1H), 1.61 (d, J=7.0 Hz, 3), 1.02-1.00 (m, 2H), 0.69-0.66 (m, 2H). MS: Calcd.: 400. Found: [M+H]+ 401.

Source