Hydrochloric Acid → 1-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochloride

1.25 M HCl in MeOH (3.0 mL) was added to tert-butyl 10-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (32 mg, 0.060 mmol), and the resulting solution was stirred under N2 at ambient temperature for 18 h. The solution was concentrated under reduced pressure, the resulting residue was diluted with MeOH (1 mL) and Et2O (10 mL), and the solids were collected by filtration to provide the title compound (31 mg, quant.) as a yellow powder: mp 310-314° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.19 (s, 2H), 9.15 (dd, J=1.0, 1.0 Hz, 1H), 8.41-8.35 (m, 2H), 8.09 (d, J=8.5 Hz, 1H), 8.05 (d, J=7.0 Hz, 1H), 7.43 (d, J=8.5 Hz, 1H), 7.30 (d, J=2.0 Hz, 1H), 7.12 (dd, J=7.0, 2.0 Hz, 1H), 3.76 (s, 3H), 3.42-3.40 (m, 2H), 3.36-3.32 (m, 2H), 3.30-3.28 (m, 2H, overlaps with H2O), 3.17 (t, J=6.5 Hz, 2H); ESI MS m/z 440 [M+H]+; HPLC (Method A) 98.83% (AUC), tR=13.9 min.

1. concentrationThe solution was concentrated under reduced pressure
2. additionthe resulting residue was diluted with MeOH (1 mL) and Et2O (10 mL)
3. filtrationthe solids were collected by filtration

ORD record

ord-85fa752a09314e998c23c3f86391ce2b

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637501B2