Benzophenone imine → 2-(6-Amino-2,3-dihydro-4h-1,4-benzoxazin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydro-4h-[1,3]thiazolo[5,4-c]azepin-4-one

Participants

Reaction Steps

A mixture of Example 67 (0.48 g, 0.98 mmol), benzophenone imine (0.356 g, 1.96 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (40 mg, 0.06 mmol), sodium tert-butoxide (0.192 g, 2.0 mmol) and tris(dibenzylidineacetone)dipalladium(0) (29 mg, catalytic) in THF (10 mL) was heated to 120° C. for 2 h. The reaction mixture was cooled to r.t., concentrated in vacuo, and the residue dissolved in methanol (2 mL). 2N Hydrochloric acid (10 mL) was added and the mixture stirred overnight. It was basified with aqueous sodium carbonate and extracted with DCM (3×25 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was triturated with Et2O to give the title compound (0.30 g, 89%) as a beige solid. δH (CDCl3) 1.11 (6H, s), 2.85 (2H, s), 3.12 (2H, d, J 5.3 Hz), 3.52 (2H, br.s), 4.07-4.13 (2H, m), 4.19-4.26 (2H, m), 5.93 (1H, br.s), 6.40 (1H, dd, J 8.5, 2.6 Hz), 6.75 (1H, d, J 8.7 Hz), 7.29 (1H, d, J 2.6 Hz). LCMS (ES+) 345 (M+H)+.

Provenance & Evidence