Hydrochloric Acid → HCID 69676466, compound

Participants

Reaction Steps

A solution of (S)-tert-butyl 3-(propyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (300 mg, 0.58 mmol) in 1,4-dioxane (5 mL) was treated with 4 N HCl in 1,4-dioxane (10 mL) at rt for 1 h. The solvent was removed in vacuo and the residue was suspended in water (10 mL). The aqueous layer was adjusted to a pH 9 with solid NaHCO3 and the solution was extracted with EtOAc (3×25 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo to yield titled intermediate (241 mg, 83%), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.23 (1s, 1H), 7.98 (d, J=8.0 Hz, 2H), 7.69 and 7.65 (2d, 0.1=4.0 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 6.81 (d, J=4.0 Hz, 1H), 3.69-3.64 (m, 3H), 3.51-3.47 (m, 2H), 3.25-3.18 (m, 2H), 52.85-2.83 (m, 1H), 2.35 (s, 3H), 1.94-1.89 (m, 2H), 1.79-1.76 (m, 1H), 1.55-1.53 (m, 1H), 1.16 and 0.93 (t, J=7.2 Hz, 3H). LC-MS: m/z [M+1]=414.

Provenance & Evidence