Hydrochloric Acid → 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

To 1,1-dimethylethyl 4-(4-amino-5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate (230 mg, 0.406 mmol) were added 1,4-Dioxane and 4N HCl in dioxane (4 mL, 16.00 mmol). The mixture was allowed to stir overnight at 50° C. The reaction was concentrated. The solid was sonicated with 1:1 Hexane:DCM and the solid was isolated by filtration to isolate 5-{1-[(3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (188 mg, 80% yield) as a white solid as the trihydrochloride salt. LC-MS (ES) m/z=467.4 [M+H]+. 1H NMR (400 MHz, METHANOL-d4) δ 8.38 (s, 1H), 8.29 (d, J=8.34 Hz, 1H), 7.61 (s, 1H), 7.41 (s, 1H), 7.35 (dd, J=1.77, 8.34 Hz, 1H), 7.22-7.28 (m, 1H), 7.18 (s, 1H), 7.13 (t, J=7.33 Hz, 2H), 5.07-5.18 (m, 1H), 4.25 (t, J=8.46 Hz, 2H), 3.90 (s, 2H), 3.68 (s, 2H), 3.61-3.67 (m, 2H), 3.25-3.31 (m, 3H), 2.41-2.54 (m, 2H), 2.36 (s, 3H), 2.34 (br. s., 2H).

Provenance & Evidence