Hydrochloric Acid → (S)-8-((2-amino-4-methylpentyl)oxy)benzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398287Notes

Reaction equation

[CH3:1][CH:2]([CH3:30])[CH2:3][C@H:4]([NH:22]C(=O)OC(C)(C)C)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][C:11]=2[CH:21]=1.Cl>ClCCl>[NH2:22][C@@H:4]([CH2:3][CH:2]([CH3:30])[CH3:1])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[NH:12][C:11]=2[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-tert-butyl (4-methyl-1-((5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (10 mg, 0.024 mmol) in dichloromethane (1 mL) was cooled to 0° C. To the solution was added hydrogen chloride (0.886 mg, 0.012 mL, 0.024 mmol, 2M in diethyl ether) dropwise. The temperature of the reaction mixture was maintained at 0° C. for 30 min and then the reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was then concentrated under reduced pressure to afford (S)-8-((2-amino-4-methylpentyl)oxy)benzo[c][2,7]naphthyridin-5(6H)-one (4 mg, 0.012 mmol, 49% yield) as a pale yellow solid. LC/MS (ESI) m/e 312.2 [(M+H)+, calcd for C18H22N3O2 312.2]; LC/MS retention time (method A): tR=1.1 min; HPLC retention time (method A): tR=6.85 min; HPLC retention time (method B): tR=7.51 min 1H NMR (400 MHz, D2O) δ ppm 9.30 (br. s., 1H), 8.77 (br. s., 1H), 8.36 (br. s., 1H), 8.07 (br. s., 1H), 6.95 (br. s., 1H), 6.72 (br. s., 1H), 4.41 (d, J=9.03 Hz, 1H), 4.26 (br. s., 1H), 3.89 (br. s., 1H), 3.38 (s, 1H), 1.72-1.88 (m, 2H), 1.05 (d, J=2.51 Hz, 6H).

Workup

temperatureto warm to room temperature
concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record: ord-e1c75d54eb42422e8d6723b467862887
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

Loading…