Hydrochloric Acid → HCID 66829882, compound

Participants

Reaction Conditions

Reaction Steps

411 f) 2-[5-Chloro-2-(5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]benzamide (CEP-19626). A solution of 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methylbenzamide (58 mg, 0.20 mmol) and 8-amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (35 mg, 0.20 mmol) in 2-methoxyethanol (5 mL) was treated with 4N HCl in 50% H2O/dioxane (50 μL, 1 equiv.) and the mixture was stirred and heated to 110° C. After 22 hrs. the mixture was cooled to room temperature, neutralized with triethylamine and concentrated. Flash chromatography (silica gel, 20% MeOH/DCM) gave 35 mg of the title compound as a pale amber solid; m.p. 232-237° C.; MS: m/z=438/440 (M+H)+, Cl-isotope pattern; 1H-NMR (DMSO-d6, δ): 11.69 (s, 1H), 9.43 (s, 1H), 8.84 (d, 8 Hz, 1H), 8.76 (s, 1H), 8.22 (s, 1H), 7.76 (d, 7 Hz, 2H), 7.67 (d, 8 Hz, 1H), 7.48 (m, 2H), 7.15 (t, 8 Hz, 1H), 7.03 (s, 1H), 6.90 (d, 9 Hz, 1H), 3.10 (m, 2H), 2.82 (s, 3H), 2.60 (m, 2H).

Provenance & Evidence