Ammonium Acetate → 1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]pyrrolidine-3-carbonitrile
Reaction equation
[C:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:21])[CH:5]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[NH2:28][CH:1]([C:4]1[C:13]([N:14]2[CH2:18][CH2:17][CH:16]([C:19]#[N:20])[CH2:15]2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[C:6]([Cl:21])[CH:5]=1)[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidine-3-carbonitrile (0.016 g, 0.053 mmol) and ammonium acetate (0.0411 g, 0.534 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.010 g, 0.16 mmol) was added. 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 C16H18ClN4 (M+H)+: m/z=301.1; Found: 301.1.
Workup
- temperatureAfter cooling to room temperature
- 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-894e2314a37b480c8159f371c9f86779
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680108B2
Reaction notes
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