Ammonium Chloride → HCID 178433735, compound

Participants

Reaction Steps

In a 5 mL microwave vial was added in 2-methyl-5-(4-morpholinyl)-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine-7-carbonitrile (60 mg, 0.156 mmol), sodium azide (81 mg, 1.252 mmol) and ammonium chloride (67.0 mg, 1.252 mmol) in N,N-Dimethylformamide (DMF) (2 mL). The reaction was subjected to MW irradiation at 180° C. for 15 min. The reaction mixture was added to a saturated NH4Cl solution and extracted with DCM (30 mL×2). The combined organic phases were dried and concentrated. The residue was purified on silica column (20˜60% EtOAc/Hexane) and then (0˜10% MeOH/DCM) to give the titled product (22 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H) 3.70 (m, 8H) 4.38 (s, 2H) 7.12 (br. s., 1H) 7.29-7.45 (m, 2H) 7.47-7.57 (m, 2H) 7.77 (d, J=8.08 Hz, 1H) 7.85-7.96 (m, 1H) 8.49 (m, 1H); LC/MS: MS (ES+) m/e 427.0 [M+H]+.

Provenance & Evidence