Hydrochloric Acid → 4-[4-(3-Methyl-3H-benzimidazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butylamide

Participants

Reaction Steps

Into the solution of 4-{4-[3-(1H-imidazol-2-yl)-phenylamino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (EXAMPLE 279) (59.4 mg, 0.118 mmol) in methanol (1.0 mL) was added HCl in methanol (9 M, 1.0 mL). The above mixture was stirred at rt for 4 h. After that time, the mixture was concentrated in vacuo and suspended in DMF (2 mL). Into the above suspension were added triethylamine (159 μL, 1.18 mmol) and tert-butyl isocyanate (14.8 μL, 0.130 mmol). The above mixture was stirred at rt under of N2 for 1 h and concentrated in vacuo to obtain a brown oil that was purified using the mass-directed purification system to yield the title compound. 1H NMR (CD3OD, 400 MHz): δ=1.37 (s, 9H), 2.56 (brs, 2H), 3.61 (t, 2H, J=4.8 Hz), 3.90 (s, 3H), 4.07 (brs, 2H), 5.69 (s, 1H), 6.29 (brs, 1H), 6.62 (s, 1H), 7.43 (dd, 1H, J=2.0 & 8.8 Hz), 7.63 (d, 1H, J=8.8 Hz), 8.08 (s, 1H), 8.11 (d, 1H, J=2.0 Hz), 8.22 (s, 1H). MS (ES+): m/z 445.11 (100) [MH+]. HPLC: tR=2.00 min (ZQ2000, polar—5 min).

Provenance & Evidence