Triethylamine → 1-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-3-pyrrolidinecarbonitrile hydrochloride
Reaction equation
[Cl:1][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:6]=[N:5][N:4]=1.[NH:18]1[CH2:22][CH2:21][CH:20]([C:23]#[N:24])[CH2:19]1.C(N(CC)CC)C>C(#N)C>[ClH:1].[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([N:7]2[C:3]([CH2:2][N:18]3[CH2:22][CH2:21][CH:20]([C:23]#[N:24])[CH2:19]3)=[N:4][N:5]=[N:6]2)[CH:13]=[CH:12][CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Preparative procedure: To a solution of 5-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole (200 mg, 0.762 mmol, commercially available from Otava, Kiev, Ukraine) in acetonitrile (4 mL) was added 3-pyrrolidinecarbonitrile (202 mg, 1.52 mmol, J&W Pharmlabs, Levittown, USA) and triethylamine (0.329 mL, 2.36 mmol). The reaction mixture was heated at 120° C. for 20 minutes in a microwave reactor. The reaction mixture was cooled then the solvent removed under vacuum. The residue was purified by MDAP. Fractions containing the desired product were combined and the solvent removed. The product was dissolved in 1 ml of DCM and 0.5 ml of 1M HCl in ether was added. Solvent was removed and the product was dried in a vacuum oven over the weekend to afford the title compound as a white solid (170 mg).
Workup
- temperatureThe reaction mixture was cooled
- customthe solvent removed under vacuum
- customThe residue was purified by MDAP
- additionFractions containing the desired product
- customthe solvent removed
- dissolutionThe product was dissolved in 1 ml of DCM
- addition0.5 ml of 1M HCl in ether was added
- customSolvent was removed
- customthe product was dried in a vacuum oven over the weekend
Sources & evidence
- ORD record
- ord-ae4474ab72dd4efca9cadbf9cad63df8
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
Loading…