Diisopropylethylamine → HCID 131735497, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 160e (20 g, 66 mmol), 4-(tert-butyl)benzene-1,2-diamine 160f (10.8 g, 66 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (30 g, 79 mmol) and diisopropylethylamine (17 g, 132 mmol) in N,N-dimethylformamide (1000 mL) was stirred at 19° C. for 12 h. See FIG. 5. TLC (petroleum ether:ethyl acetate=1:1) showed that the starting material was completely consumed. The mixture was diluted with water (1000 mL) and extracted with EtOAc (1000 mL×2). The combined organic layers were washed with brine (500 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=1:1) to afford N-(2-amino-4-(tert-butyl)phenyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropicolinamide 160g (20 g, 67%) as a yellow solid.

Provenance & Evidence