Tetrahydrofuran → 1-[5-Chloro-8-(4-cyclobutylpiperazin-1-yl)quinolin-7-yl]ethanamine

HRID 1192620Notes

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][N:18]([CH:21]3[CH2:24][CH2:23][CH2:22]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:31].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:31])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][N:18]([CH:21]3[CH2:24][CH2:23][CH2:22]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-cyclobutylpiperazin-1-yl)quinolin-7-yl]ethanone (0.0692 g, 0.201 mmol) and ammonium acetate (0.155 g, 2.01 mmol) in methanol (0.8 mL) and acetonitrile (0.8 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 (0.50 mL, 0.50 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 C19H26ClN4 (M+H)+: m/z=345.2; Found: 345.1.

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-9e7f50f27b5740cea2d5ba172279947e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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