HCID 11690537, compound → HCID 11508914, compound

Participants

Reaction Steps

Alternative solvents for removal of the Boc group include, but are not limited to, MeOH and water, as demonstrated here with EXAMPLE 45: A suspension of tert-butyl 4-[4-(1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (670 mg, 1.55 mmol) in 4 N HCl (aq) (20 mL) was stirred at rt for 18 h. The precipitates were collected by filtration and washed with ether (3×10 mL) to afford (1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine as tri-HCl salt. 1H-NMR (DMSO-d6, 400 MHz): δ=2.63 (m, 2H), 3.30 (m, 2H), 3.79 (m, 2H), 6.52 (s, br, 1H), 7.44 (dd, J=2.0, 8.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.95 (s, 1H), 8.18 (d, J=1.2 Hz, 1H), 8.26 (s, 1H), 9.59 (s, 1H). MS (ES+): m/z 332.12 [MH+]. HPLC: tR=0.44 and 1.37 min (ZQ2000, polar—5 min).

Provenance & Evidence