Dichloromethane → HCID 118207704, compound

Participants

Reaction Steps

To a 100 mL pear flask was added tert-butyl (1S,4S)-5-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (220 mg, 0.44 mmol) in dichloromethane (4.5 mL) to give a solution. To this solution was added TFA (1.5 mL). The mixture was stirred at room temperature for 30 minutes. All the volatiles were removed in vacuo, and the residue was re-suspended in toluene and concentrated to remove residual TFA. The residue was then diluted in ACN and water (total of about 90 mL), followed by the addition of 2 N HCl (4 mL). The mixture was lyophilized to give an HCl salt of the title compound as a yellow-green solid (160 mg, 78%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.67 (d, J=7.07 Hz, 3H), 2.00 (d, J=10.61 Hz, 1H), 2.33 (br s, 1H), 2.43 (s, 3H), 3.09-3.25 (m, 1H), 3.45 (d, J=10.11 Hz, 2H), 3.96-4.06 (m, 4H), 4.10-4.18 (m, 1H), 4.49 (br s, 1H), 5.95 (quin, J=6.88 Hz, 1H), 6.78 (d, J=2.27 Hz, 1H), 7.76 (br s, 1H), 8.03 (br s, 1H), 8.25 (br s, 1H), 8.63 (br s, 1H), 9.08 (br s, 1H), 9.78 (br s, 1H), 10.19 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C21H25N9, 404. found 404.

Provenance & Evidence