Réaction #2161269

Équation de réaction

NaBH(OAc)3

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine

acetone

→

title compound

Rendement 57.4%

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}-N-isopropylpiperidin-4-amine

Rendement 57.4%

Solvants

CH2Cl2

NaOH

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction mixture was stirred overnight at room temperature
2. 2
   workup.STIRRINGthe bi-phasic solution was stirred for 20 minutes
3. 3
   ExtractionThe mixture was extracted with CH2Cl2 (2×25 mL)
4. 4
   Séchagethe combined organic layers were dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH)

Mode opératoire

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (0.3 g, 0.76 mmol) in CH2Cl2 (5 mL) was added acetone (56 μL, 0.76 mmol) and the solution was stirred for 15 minutes at room temperature. This was followed by the addition of NaBH(OAc)3 (0.242 g, 1.14 mmol) and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with CH2Cl2 (20 mL) and 2 M NaOH and the bi-phasic solution was stirred for 20 minutes. The mixture was extracted with CH2Cl2 (2×25 mL) and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to give the title compound as a white solid (0.19 g, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 8.51 (d, 2 H), 7.66 (d, 2 H), 7.30 (t, 2 H), 7.14 (t, 2 H), 6.51 (s, 1 H), 5.13-5.20 (m, 2 H), 4.07-4.16 (m, 1 H), 3.93 (s, 2 H), 3.77-3.87 (m, 1 H), 3.04-3.14 (m, 1 H), 2.83-2.93 (m, 1 H), 2.69-2.79 (m, 2 H), 1.72-1.86 (m, 5H); m/z (APCI+) for C25H30N5OF 436.1 (M+H)+.

Source