Triethylamine → 4-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine

HRID 705706

반응식

HRID 705706 반응식
Cl[C:2]([C:16]([F:19])([F:18])[F:17])=[C:3]([C:6]1[CH:14]=[C:13]([Cl:15])[C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1)[C:4]#[N:5].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[NH:26][NH2:27].C(N(CC)CC)C>C(O)C>[Cl:15][C:13]1[C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=[C:6]([C:3]2[C:2]([C:16]([F:18])([F:17])[F:19])=[N:27][N:26]([C:21]3[N:22]=[CH:23][CH:24]=[CH:25][N:20]=3)[C:4]=2[NH2:5])[CH:14]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 3465582-HydrazinylpyrimidineHCID 1317336953-Chloro-2-(7-chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-but-2-enenitrile

생성물 1

HCID 900100644-(7-Chloro-1,3-benzodioxol-5-yl)-2-pyrimidin-2-yl-5-(trifluoromethyl)pyrazol-3-amine수율 44%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

3-chloro-2-(7-chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-but-2-enenitrile (20.2 g, 65.4 mmol) was dissolved in ethanol (200 mL) and treated with pyrimidin-2-yl-hydrazine (7.20 g, 65.4 mmol) and triethylamine (6.60 g, 65.4 mmol). The reaction mixture was heated to reflux for 10 h. The solvent was removed in vacuo, to the residue was added water, extracted with EtOAc, then the organic layer was combined, washed with water and brine, dried, filtered and concentrated to give crude product. The crude product was washed with DCM to give the title compound (11.0 g; 44%).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 10 h
  3. customThe solvent was removed in vacuo, to the residue
  4. additionwas added water
  5. extractionextracted with EtOAc
  6. washwashed with water and brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product
  11. washThe crude product was washed with DCM

출처 및 근거

ORD 기록
ord-ad6ad92f945645c5a0d9b2db56f7291b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174967B2

연결된 노트

불러오는 중…