Thiazole → HCID 58709960, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a solution of tert-butyl 4-[4-(3-iodo-4-methoxyphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (109.5 mg, 0.2 mmol), thiazole (85.1 mg, 1.0 mmol), potassium acetate (39.3 mg, 0.4 mmol), and tetrakis(triphenylphosphine)-palladium (23.1 mg, 0.02 mmol) in DMF (0.8 mL) for 3 min. The mixture was then heated to 100° C. and stirred for 17 h. The solvents were removed in vaccuo and the residue was dissolved in DMF (−2 mL). The DMF solution was filtered and sent to mass-directed HPLC purification to give the title compound. 1H-NMR (CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.55 (m, 2H), 3.66 (m, 2H), 3.98 (s, 3H), 4.13 (m, 2H), 6.28 (s, br, 1H), 6.60 (s, 1H), 7.17 (d, J=9.2 Hz, 1H), 7.68 (dd, J=2.4, 8.8 Hz, 1H), 8.06 (d, J=2.8 Hz, 1H), 8.20 (s, 1H), 8.31 (s, 1H), 8.98 (s, 1H). MS (ES+): m/z 504.99 (MH+). HPLC: tR=2.95 min (ZQ2000, polar—5 min). The following EXAMPLES 300-301 are compounds of Formula (I) wherein X=C—CN.

Provenance & Evidence