Tetrahydrofuran → HCID 58368417, compound

HRID 1192632Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:34])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[5-chloro-8-(4-phenoxypiperidin-1-yl)quinolin-7-yl]ethanone (0.0236 g, 0.0620 mmol) and ammonium acetate (0.0478 g, 0.620 mmol) in methanol (0.3 mL) and acetonitrile (0.3 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 (0.15 mL, 0.15 mmol). The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C22H25ClN3O (M+H)+: m/z=382.2; Found: 382.2.

Workup

temperatureAfter cooling to room temperature, to the resulting mixture
temperatureThe reaction was heated at 65° C. overnight
temperatureThe mixture was cooled to room temperature
customquenched with sat. NaHCO3 solution
extractionextracted with dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-f41498e7ae31413586ef226262240ed3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…