Triethylamine → 6-bromo-4-(((3aS,4R,5R,6aS)-2-(2-hydroxy-2-methylpropanoyl)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

Participants

Reaction Steps

A mixture of 6-bromo-4-(((3aS,4R,5R,6aS)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide TFA salt from Step 2 of Example 59 (151 mg, 0.307 mmol), 2-hydroxy-2-methylpropanoic acid (38.3 mg, 0.368 mmol), triethylamine (0.128 mL, 0.920 mmol) and (benzotriazol-1-yloxy)tris(dimethylamine)phosphonium hexafluorophosphate (163 mg, 0.368 mmol) in dimethylformamide (2 mL) was stirred at room temperature for 2 h. The mixture was diluted with ethyl acetate (80 mL), washed with saturated sodium bicarbonate, water, brine, dried (MgSO4) and concentrated to give the expected product (120 mg). 1H NMR (400 MHz, methanol-d4) d 8.13 (s, 1H), 7.63 (d, J=1.8 Hz, 1H), 7.03 (d, J=1.8 Hz, 1H), 4.35-4.03 (m, 2H), 3.99-3.51 (m, 3H), 2.88-2.79 (m, 1H), 2.72-2.66 (m, 2H), 1.82-1.61 (m, 2H), 1.47-1.39 (m, 6H), 1.16 (d, J=6.6 Hz, 3H); MS (ES+) m/z: 436.1, 438.2 (M+H); LCMS (M+1): 464.1, 466.2.

Provenance & Evidence