Ammonia → HCID 58529910, compound

Participants

Reaction Steps

A solution in THF (1 mL) containing 5-(2-benzyl-2H-indazol-6-yl)-7-morpholin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (170 mg, 0.315 mmol), (1H-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (209 mg, 0.47 mmol), N-methylmorpholine (111 mg, 1.1 mmol) and N,N-dimethylglycine hydrochloride (65.9 mg, 0.47 mmol) was stirred at rt for one hour. The reaction was diluted with 1 mL MeOH and treated with 25% sodium methoxide solution in MeOH (100 uL, 2 mmol). After an additional 30 min stirring at rt, the reaction was partitioned between EtOAc and 2N sodium carbonate solution. The organic phase was separated, dried with sodium sulfate and concentrated in vacuo to provide a dark orange solid. This material was taken up in 9.5 mL CH2Cl2 and 0.5 mL 7N NH3 in MeOH. The resulting solution was filtered through a silica plug (pretreated with NH3) and the volatiles removed in vacuo. Trituration of the resulting solid with ether provided 114 mg (71%) of the desired product as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1 H), 7.98 (d, 1 H, J=4 Hz)), 7.60 (s, 1 H), 7.50-7.60 (m, 2H), 7.14 (d, 1H, J=7 Hz), 6.80 (s, 1H), 7.27-7.41 (m, 5H), 5.65 (s, 2H), 4.89-5.06 (m, 1H), 4.18-4.52 (m, 2H), 3.86-4.04 (m, 2H), 3.21-3.65 (m, 2H), 3.30 (s, 2H), 2.19 (s, 3H), 2.15 (s, 3H); ES-MS m/z 511.3 [M+H]+, HPLC RT (min) 2.12 min.

Provenance & Evidence