Diisopropylethylamine → HCID 89768550, compound

Participants

Reaction Steps

2-(3-nitrophenyl)ethanamine hydrochloride (100.00 mg; 0.49 mmol; 1.00 eq.), 6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (SYN5052A) (174.06 mg; 0.49 mmol; 1.00 eq.), o-(7-azabenzotriazol-1-yl)-n,n,n′,n′-tetra-methyluronium hexafluorophosphate (375.28 mg; 0.99 mmol; 2.00 eq.) and N-ethyl-N-isopropylpropan-2-amine (0.32 ml; 1.97 mmol; 4.00 eq.) are placed into a scintillation vial equipped with a stir bar. The mixture is taken up in DMF (3.00 ml). The reaction mixture is stirred for 16 hours. Upon completion, the reaction mixture is diluted with ethyl acetate (100 mL) and extracted with brine solution. The organic layer is then dried over magnesium sulfate, filtered, concentrated and purified via Prep HPLC using a gradient of 10-50% acetonitrile in water with 0.1% trifluoroacetic acid modifier to give 6-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methyl-N-[2-(3-nitrophenyl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxamide (10) (226.4 mg; 0.45 mmol; 91.6%);

Provenance & Evidence