4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59199967, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (300 mg, 1.38 mmol) and 4-(1-amino-5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol (325 mg, 1.38 mmol) in DMF (5 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (380 mg, 1.38 mmol) and stirred at 50° C. for 2 h. The mixture is diluted with saturated aqueous Na2CO3 (50 mL), and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0%-7% MeOH in DCM to afford 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide (200 mg, 33%). MS: 435 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.26 (s, 1H), 9.09 (d, 2H), 7.70 (t, 1H), 7.29 (m, 2H), 7.22 (s, 1H), 7.01 (m, 1H), 2.90 (s, 3H), 2.82 (m, 2H), 1.91 (m, 2H), 1.31 (s, 6H).

Provenance & Evidence