Sodium Carbonate → HCID 178489736, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R,Z)-methyl 2-(2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylideneaminooxy)acetate (105c, 175 mg, 0.4 mmol), 2-(6-methoxypyridin-2-yl)-6-phenyl-1,3,6,2-dioxazaborocane (298 mg, 1.0 mmol), Pd(dppf)2Cl2 (32.5 mg, 0.04 mmol), 2N Na2CO3 (1.0 mL, 2.0 mmol) in DMA (3 mL) was degassed with N2 and heated at 85° C. for over night. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and filtered through celite. The filtrate was concentrated to afford brown oil which was purified by preparative LCMS to afford (R,Z)-2-(2-amino-7-(4-fluoro-2-(6-methoxypyridin-2-yl)phenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-ylideneaminooxy)acetic acid (105d, 56 mg, 31%) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.79 (s, 3H) 3.16 (dd, J=17.05, 10.48 Hz, 1H) 3.45 (dd, J=17.05, 3.92 Hz, 1H) 3.88 (s, 3H) 4.59 (d, J=3.03 Hz, 2H) 4.96 (dd, J=10.36, 3.79 Hz, 1H) 5.90 (brs, 1H) 6.76 (d, J=8.34 Hz, 1H) 7.02 (d, J=6.82 Hz, 1H) 7.14 (dd, J=9.09, 2.78 Hz, 1H) 7.19 (td, J=8.34, 2.78 Hz, 1H) 7.62 (dd, J=8.59, 5.56 Hz, 1H) 7.68 (dd, J=8.34, 7.33 Hz, 1H). MS (ES) [M+H] calculated for C22H22FN6O4, 453.16. found 453.30.

Provenance & Evidence