4-Methylmorpholine → HCID 66640695, compound

Participants

Reaction Conditions

Reaction Steps

To the above ester in MeOH/THF (10:5) (15 mL) was added 3N NaOH (5.0 mL) and stirred at 60° C. After 14 hours. The reaction mixture was concentrated, diluted with water and washed with ether (30 mL). The aqueous phase was then neutralized with 6 N HCl (1.5 mL), extracted with ethyl acetate, and then dried (MgSO4). Filtration and concentration gave the acid which was used further without purification. MS found for C17H19N5O2S as (M+H)+ 358.24. To the above acid (70 mg, 0.2 mmol) in DMF (2 mL), was added HATU (114 mg, 0.3 mmol), (3-amino-4′-fluoro-biphenyl-4-yl)-carbamic acid tert-butyl ester (118 mg, 0.4 mmol) and NMM (0.1 mL, 0.78 mmol) and stirred at 50° C. for 16 hours. The reaction mixture was diluted with water and acetonitrile. The resulting solid was filtered, washed with water, and dried to give [4′-fluoro-3-({5-[4-(3-isopropyl-2-methyl-3H-imidazol-4-yl)-pyrimidin-2-ylamino]-4-methyl-thiophene-2-carbonyl}-amino)-biphenyl-4-yl]-carbamic acid tert-butyl ester. MS found for C34H36FN7O3S as (M+H)+ 642.02.

Provenance & Evidence