Sodium hydride → 9-{[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]methyl}-3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine

Participants

Reaction Steps

NaH (65 mg, 0.28 mmol) was added to a solution of 3-pyridin-4-yl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a][1,3]diazepine (54 mg, 0.25 mmol) in DMF (5 ml). After 10 min 3-(chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (65 mg, 0.28 mmol) was added at r.t. Stirring was continued o.n. and NH4Cl solution, sat., was added and the mixture was extracted with EA. The organic phase was dried and concentrated. Flash chromatography (DCM/MeOH 20:1) yielded 56 mg (54%) of the title compound. 1H NMR: 1.89-2.01 (m, 4H), 3.33-3.42 (m, 2H), 3.90-3.98 (m, 2H), 4.88 (s, 2H), 7.42-7.49 (m, 3H), 7.53 (m, 1H), 7.98 (m, 1H), 8.09 (m, 1H), 8.71 (d, 2H).

Provenance & Evidence