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

HRID 705706

反応式

HRID 705706 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ad6ad92f945645c5a0d9b2db56f7291b
出典データセット
uspto-grants-2015_11
特許番号
US09174967B2

関連ノート

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