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

HRID 517762노트

반응식

HRID 517762 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ae4474ab72dd4efca9cadbf9cad63df8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115132B2

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