Cyclopentylamine → HCID 76852923, compound

Participants

Reaction Steps

7-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (Example 138) (75 mg, 0.42 mmol) and cyclopentylamine (45 μL, 0.46 mmol) were dissolved in methanol (3 mL). After 4 h, sodium borohydride (25 mg, 0.67 mmol) was added in one portion. After an additional 2 h, the reaction mixture was quenched by addition of 2 N aqueous sodium hydroxide and extracted with diethyl ether. The organic layer was dried over sodium sulfate and evaporated. The residue was dissolved in acetonitrile and salted with 1 N ethereal hydrochloric acid. The precipitate was collected by filtration and crystallized from acetonitrile to give N-[(7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]-N-cyclopentylamine hydrochloride (35 mg, 30%) as a white solid: mp 241-244° C.; 1H NMR (300 M-z, CD3OD) δ1.70-1.95 (6H, m), 2.25 (2H, m), 3.75 (1H, m), 4.57 (2H, s), 7.09 (1H, s), 7.93 (1H, d, J=6.0 Hz), 8.12 (1H, J=6.0 Hz); ESI MS m/z 250 [C13H16ClN3+H]+; HPLC (Method C) >99% (AUC), tR=12.9 min.

Provenance & Evidence