Reaktion #2264765

Reaktionsgleichung

HATU

1-phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine

2-chloro-3-(trifluoromethyl)benzoic acid

Et3N

→

5-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-1-phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine

Ausbeute 92.5%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to minimum volume
2. 2
   Sonstigepurified on 16 g SiO2 with 0-3.5% NH3 in MeOH/CH2Cl2

Vorschrift

A solution of 1-phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine (17 mg, 0.085 mmol) and 2-chloro-3-(trifluoromethyl)benzoic acid (21 mg, 0.093 mmol) in DCM (8 mL) was treated with Et3N (35 μL, 0.25 mmol) followed by HATU (38 mg, 0.1 mmol). The reaction was stirred overnight, then concentrated to minimum volume and purified on 16 g SiO2 with 0-3.5% NH3 in MeOH/CH2Cl2 to give 32 mg (91%) of 5-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-1-phenyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine. MS (ESI): mass calcd. for C19H14ClF3N4O, 406.1. m/z found, 407.1 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 7.84-7.75 (m, 1H), 7.62-7.43 (m, 7H), 5.11 (q, J=16.5 Hz, 1H), 4.64-4.45 (m, 1H), 4.32 (dt, J=13.2, 5.4 Hz, 0.5H), 4.05-3.95 (m, 0.5H), 3.65-3.48 (m, 1H), 3.04 (t, J=5.9 Hz, 1H), 3.01-2.76 (m, 1H).

Quelle