tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate → HCID 178434298, 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 (50.1 mg, 0.150 mmol) and 3-methyl-1H-indazol-5-ylamine (25.0 mg, 0.170 mmol) in iPrOH (2.5 mL) in a sealed tube was heated to 90° C. (bath temp.) for 16 h. The solvent was evaporated, water/NaHCO3 solution was added, the mixture was extracted with CH2Cl2 (3×30 mL), and the combined extracts were washed with brine and dried over MgSO4. The extracts were filtered through a pad of silica gel, washing with 5% MeOH in CH2Cl2 until no more product eluted as indicated by TLC. Concentration in vacuo gave a light brown solid. The solid was triturated with MeOH, filtered, washed with more MeOH, and dried in vacuo overnight. One obtained the title compound as white solid, mp. 245-250° C. (decomp.). 1H NMR (DMSO-d6, 400 MHz): δ=1.43 (s, 9H), 2.42-2.50 (brs, 2H), 2.47 (s, 3H), 3.53-3.59 (me, 2H), 3.99-4.08 (m, 2H), 6.38 (brs, 1H), 6.73 (brs, 1H), 7.43 (d, J=8.8 Hz, 1H), 7.69 (dd, J=1.6, 8.8 Hz, 1H), 8.15 (s, 1H), 8.23 (s, 1H), 9.32 (s, 1H), 11.88 (brs, 1H), 12.54 (s, 1H). MS (ES+): m/z 446.0 (100) [MH+]. HPLC: tR=2.4 min (ZQ2000, polar—5 min).

Provenance & Evidence