2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → 7-cyclopentyl-N,N-dimethyl-2-(5-(cis-6-oxotetrahydro-1H-pyrrolo[3,4-c]pyridin-5(6H,7H,7aH)-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Participants

Reaction Steps

Following general N—C coupling procedure 1, 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide and cis-tert-butyl 5-(6-aminopyridin-3-yl)-6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate were combined and gave after purification cis-tert-butyl 5-(6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)pyridin-3-yl)-6-oxohexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (81 mg) in 86% yield. 1H NMR (400 MHz, CDCl3) δ ppm 8.79 (s, 1H), 8.56 (s, 1H), 8.53 (s, 1H), 8.24 (d, J=2.53 Hz, 1H), 7.63 (dd, J1=9.09 Hz, J2=2.53 Hz, 1H), 6.46 (s, 1H), 4.81 (m, 1H), 3.84 (dd, J1=13.14 Hz, J2=5.56 Hz, 1H), 3.78-3.63 (m, 3H), 3.49-3.21 (m, 2H), 3.16 (s, 6H), 2.79 (m, 3H), 2.55 (m, 3H), 2.07 (m, 4H), 1.72 (m, 2H), 1.48 (s, 9H). LCMS m/z 589.6 (M+H)+.

Provenance & Evidence