Hydrochloric Acid → HCID 86687704, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial charged with Pd(Amphos)2Cl2 (0.008 g, 0.012 mmol), 2-methoxyphenylboronic acid (0.036 g, 0.234 mmol), 1-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (From example 160; 0.050 g, 0.117 mmol), potassium phosphate (0.099 g, 0.469 mmol), 1.5 mL dioxane, and 0.25 mL water was heated to 150° C. in the microwave for 30 minutes. LC/MS showed mostly product, so the aqueous layer was removed and the reaction mixture was treated with HCl (4N in dioxane) (117 μl, 0.469 mmol). After stirring for 10 minutes, the reaction mixture was concentrated. The crude residue was purified by [PREP LC/MS-2 System Column: XBridge 19×100 mm 12230326114 03 Mobile phase: 0.1% NH4OH in water/acetonitrile Flow rate: 40 ml/min Inj: 2200 uL. Gradient: 10 min10-40%_LV_NH3] yielding 1-(2′,3-dimethoxy-[1,1′-biphenyl]-4-yl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.014 g, 0.028 mmol, 24.0%). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.67 (s, 3H) 3.79-3.88 (m, 3H) 6.99-7.13 (m, 2H) 7.17 (d, J=8.12 Hz, 1H) 7.22-7.32 (m, 2H) 7.32-7.48 (m, 3H) 7.81 (d, J=8.76 Hz, 1H) 7.98 (d, J=9.03 Hz, 1H) 8.09 (d, J=5.61 Hz, 1H) 8.26 (br. s., 1H) 8.58 (s, 1H) 8.61-8.72 (m, 2H); (M+H)+=499.3.

Provenance & Evidence