Formaldehyde → HCID 71572440, compound

Participants

Reaction Steps

To a solution of N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(octahydro-1H-pyrrolo[3,4-b]pyridin-1-yl) propoxy)quinazolin-4-amine (0.45 g) in the mixture solvent of MeOH and CH2Cl2 (1:1) was added 37% HCHO (1.00 mL) and acetic acid (0.50 mL) dropwise. The reaction mixture was stirred for 30 min at room temperature, NaB(OCOCH3)3H (1.50 g) was added in portions. The reaction mixture was stirred for another 2 h at room temperature, poured into water and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH) to give the title compound as a pale yellow solid (0.60 g, 70.00%), HPLC: 98.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 500.1 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 1.82 (m, 1H), 2.33 (m, 4H), 1.94 (m, 1H), 2.19-2.20 (m, 2H), 2.50-2.52 (m, 1H), 2.67-2.70 (m, 2H), 3.58 (s, 3H), 4.01-4.02 (m, 2H), 4.03-4.04 (m, 5H), 4.05-4.07 (m, 1H), 4.40 (s, 2H), 7.44 (s, 1H), 7.50 (t, J=4.8 Hz, 1H), 7.83-7.88 (m, 1H), 8.07-8.08 (m, 1H), 8.89-8.91 (m, 1H), 9.05 (s, 1H) ppm.

Provenance & Evidence