Dimethylformamide → HCID 86679006, compound

Participants

Reaction Conditions

Reaction Steps

A DMF (4 mL) solution containing 4-amino-2-(6-chloro-1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-N-cyclopropyl-5-methyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide, as described in Example 176, (149 mg, 0.273 mmol), zinc cyanide (19.3 mg, 0.164 mmol), 1,1′-bis(diphenylphosphino)ferrocene (15.16 mg, 0.027 mmol), and tris(dibenzylideneacetone)dipalladium (0) (12.52 mg, 0.014 mmol) was degassed for 1 hour at rt. The reaction mixture was then stirred for 15 hours at 130° C. The reaction mixture was then cooled and ethyl acetate (30 mL) and water (10 mL) were added. The water layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by reverse phase HPLC to afford the indicated product. Chiral separation using SFC on a Chiralcel OD column provided both enantiomers of the title compound. 1NMR (500 MHz, CD3COCD3): δ 0.56 (m, 2H); 0.71 (M, 2H); 1.73 (s, 3H); 2.77 (m, 1H); 3.06 (m, 2H); 5.02 (t, J=7.0 Hz, 2H); 7.00 (br, 2H); 7.52 (br, 1H); 7.84 (d, J=8.2 Hz, 1H); 9.28 (d, J=8.2 Hz, 1H). m/z=536.1 (M+H).

Provenance & Evidence