2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

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Reaction Steps

Using General Buchwald method 1, 2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (139 mg, 0.476 mmol, 1.0 eq) was combined with 3-(6-Amino-pyridin-3-yl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (145 mg, 0.476 mmol, 1.0 eq) to give 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (143 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42 (s, 9H) 1.57-1.70 (m, 2H) 1.74-1.92 (m, 4H) 1.98 (br. s., 4H) 2.36-2.48 (m, 2H) 2.78 (d, J=10.11 Hz, 2H) 3.05 (br. s., 6H) 3.48 (d, J=10.11 Hz, 2H) 4.24 (br. s., 2H) 4.73 (qd, J=8.76, 8.59 Hz, 1H) 6.59 (s, 1H) 7.37 (dd, J=9.09, 3.03 Hz, 1H) 7.94 (d, J=3.03 Hz, 1H) 8.13 (d, J=9.09 Hz, 1H) 8.75 (s, 1H) 9.24 (s, 1H); MS m/z 561.3 (M+H).

Provenance & Evidence