Ammonia → HCID 178457184, compound

Participants

Reaction Steps

A solution of {[(3aR,6R,6aS)-6-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]methyl}[4-(5-tert-butyl-1H-1,3-benzodiazol-2-yl)butyl]propan-2-ylamine, (120 mg, 0.2 mmol) in methanolic ammonia (7N, 10 ml) was heated to 80° C. in a glass walled sealed tube with stirring overnight. The reaction mixture was then concentrated in vacuo, re-treated with methanolic ammonia (7N, 10 ml) and the reaction was continued for a further 48 hrs. This was then absorbed onto silica gel and purified by silica gel column chromatography, eluting with 7N NH3 in MeOH:DCM (4:96). The product was purified further on a preparative TLC plate, eluting with 7N NH3 in MeOH:DCM (1:9) to give an off-white solid product (75 mg, 67%): MS (ESI+) for C33H47N7O2 m/z 573.79 [M+H]+; HPLC purity 98% (ret. time, 1.23 min); 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.92-8.29 (1H, m), 7.22-7.58 (2H, m), 6.58-7.08 (1H, m), 6.24-6.58 (1H, m), 4.68-5.00 (2H, m), 4.28-4.46 (2H, m), 3.21-3.33 (2H, m), 2.50-3.03 (4H, m), 2.36 (5H, d, J=5.34 Hz), 1.54-2.09 (3H, m), 1.32-1.49 (6H, m), 1.14-1.34 (9H, m), 0.71-1.01 (6H, m)

Provenance & Evidence