Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 90386162, compound

Participants

Reaction Steps

To a solution of 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinic acid (50.0 mg, 0.119 mmol) in DMF (1 mL) was added DMAP (22.0 mg, 0.178 mmol) followed by HATU (68.0 mg, 0.178 mmol) and the reaction mixture stirred for 10 minutes at room temperature. Methyl 2-amino-3-sulfamoylpropanoate (10.8 mg, 0.0590 mmol) was added and the reaction mixture stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure and water (10 mL) was added to the resulting residue and the solution extracted with DCM (2×25 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Condition B-102 as described in general methods) to obtain (methyl 2-(5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinamido)-3-sulfamoylpropanoate (10.0 mg, 27.6%). LCMS Condition B-19: retention time 2.11 min, [M+1]=586.1. HPLC Condition B-30: retention time 11.20 min, Purity 98.0%. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.65 (d, J=6.3 Hz, 2H), 3.71 (s, 3H), 4.84 (d, J=5.8 Hz, 2H), 4.93 (d, J=7.1 Hz, 1H), 6.72 (t, J=5.6 Hz, 1H), 6.83 (d, J=2.8 Hz, 1H), 7.08 (br s, 2H), 7.21-7.29 (m, 1H), 7.31-7.42 (m, 5H), 7.44-7.52 (m, 2H), 7.53-7.57 (m, 2H), 7.93 (d, J=2.8 Hz, 1H), 8.95 (t, J=2.1 Hz, 1H), 9.09 (d, J=2.1 Hz, 1H), 9.44 (d, J=7.8 Hz, 1H), 9.50 (d, J=2.1 Hz, 1H).

Provenance & Evidence