Tetrahydrofuran → 1-[5-Chloro-8-(3-methoxypyrrolidin-1-yl)quinolin-7-yl]ethanamine
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH:17]([O:20][CH3:21])[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:28].[Na+].O1CCCC1>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:28])[CH3:13])[C:9]([N:15]2[CH2:19][CH2:18][CH:17]([O:20][CH3:21])[CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 1-[5-chloro-8-(3-methoxypyrrolidin-1-yl)quinolin-7-yl]ethanone (0.0445 g, 0.146 mmol) and ammonium acetate (0.112 g, 1.46 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 (0.36 mL, 0.36 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 organic layers were combined, dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C16H21ClN3O (M+H)+: m/z=306.1; Found: 306.1.
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 materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-268ce9b9c7b74b8d8b242435e45c9465
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680108B2
Reaction notes
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