tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate → HCID 58709776, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (110 mg, 0.33 mmol) and 3-amino-1-phenethyl-1H-pyrazole (74 mg, 0.39 mmol) in 1-butanol (3 mL) was heated at 120° C. overnight, LC-MS showed the reaction was complete. The mixture was concentrated, then dissolved in MeOH-DMSO, and purified by MSDP (using water/acetonitrile/HCOOH mixtures) to give the title compound as a brown solid. LC-MS (ES, Pos.): 486 [MH+]. 1H NMR (CD3OD, 400 MHz): δ=1.49 (s, 9H), 2.54 (m, 2H), 3.16 (t, J=7.1 Hz, 2H), 3.65 (m, 2H), 4.12 (m, 2H), 4.32 (t, J=7.1 Hz, 2H), 6.27 (s, 1H), 6.48 (d, J=2.3 Hz, 1H), 6.53 (s, 1H), 7.14-7.28 (m, 5H), 7.36 (d, J=2.3 Hz, 1H), 8.21 (s, 1H).

Provenance & Evidence