Triethylamine → 1-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-3-pyrrolidinecarbonitrile hydrochloride

HRID 517762ノート

反応式

HRID 517762 の反応式
[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]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 80271755-(Chloromethyl)-1-(3-(trifluoromethyl)phenyl)-1H-tetrazoleHCID 22181493Pyrrolidine-3-carbonitrile

生成物 1

HCID 866918901-({1-[3-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-3-pyrrolidinecarbonitrile hydrochloride

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed under vacuum
  3. customThe residue was purified by MDAP
  4. additionFractions containing the desired product
  5. customthe solvent removed
  6. dissolutionThe product was dissolved in 1 ml of DCM
  7. addition0.5 ml of 1M HCl in ether was added
  8. customSolvent was removed
  9. customthe product was dried in a vacuum oven over the weekend

出典と根拠

ORDレコード
ord-ae4474ab72dd4efca9cadbf9cad63df8
出典データセット
uspto-grants-2015_08
特許番号
US09115132B2

反応ノート

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