Hydrochloric Acid → HCID 89980374, compound

Participants

Reaction Conditions

Reaction Steps

9-acetyl-2-(1-methyl-1H-pyrazol-3-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one. 47-1. A mixture of 9-iodo-2-(1-methyl-1H-pyrazol-3-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (Example 31) (2.0 g, 4.78 mmol), tributyl(1-ethoxyvinyl)stannane (2.02 mL, 5.98 mmol) and Pd(PPh3)4 (276 mg, 0.24 mmol) in 1,4-dioxane (15 mL) was heated to 140° C. for 90 min. The mixture was then filtered and concentrated in vacuo and the residue obtained was purified by flash chromatography (SiO2, DCM to DCM/MeOH 95:5). The brown oil obtained was taken up in THF (100 mL) and treated with a 0.1 N aq. solution of HCl (48 mL, 4.78 mmol). The mixture was stirred at RT for 90 min. The mixture was then diluted with AcOEt and washed with a saturated aq. solution of NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was purified by flash chromatography (SiO2, DCM to DCM/MeOH 95:5) to give a brown oil that was suspended in Et2O. The suspension was filtered and the filter cake was dried in vacuo to give the title compound (912 mg) as a yellow solid. UPLC-MS: MS 335.0 (M+H+); UPLC rt 0.62 min. 1H NMR (400 MHz, CHLOROFORM-d): δ ppm 2.62 (s, 3 H); 3.24 (t, J=6.06 Hz, 2 H); 3.81 (t, J=6.45 Hz, 2 H); 3.92 (s, 3 H); 4.49 (br. s., 2 H); 6.81 (br. s., 1 H); 7.17 (s, 1 H); 7.34-7.45 (m, 2 H); 7.77 (d, J=7.82 Hz, 1 H); 7.84 (d, J=7.82 Hz, 1 H).

Provenance & Evidence