Tetrahydrofuran → HCID 58368441, compound

HRID 1192643Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[NH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]([C:21](=O)[CH3:22])=[CH:12][C:13]([Cl:20])=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:6]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:31].[Na+].O1CCCC1>CO.C(#N)C>[CH3:1][O:2][C:3](=[O:24])[NH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]([CH:21]([NH2:31])[CH3:22])=[CH:12][C:13]([Cl:20])=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:6]1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of methyl[(3S)-1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidin-3-yl]carbamate (0.047 g, 0.14 mmol) and ammonium acetate (0.104 g, 1.35 mmol) in methanol (0.5 mL) and acetonitrile (0.5 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, to the resulting mixture was added 1.0 M sodium cyanoborohydride in tetrahydrofuran (0.34 mL, 0.34 mmol). The reaction was heated at 65° C. overnight. The mixture was then cooled to room temperature, quenched with sat. NaHCO3 solution, extracted with dichloromethane, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C17H22ClN4O2 (M+H)+: m/z=349.1; Found: 349.1.

Workup

temperatureAfter cooling to room temperature, to the resulting mixture
temperatureThe reaction was heated at 65° C. overnight
temperatureThe mixture was then cooled to room temperature
customquenched with sat. NaHCO3 solution
extractionextracted with dichloromethane
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-c144667c85b745f1900f6324ceb3392e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…