Thionyl Chloride → n-[2-[1-(2-Chlorophenyl)-3-(trifluoromethyl)-1h-pyrazol-5-yl]-8-methyl-4h-3,1-benzoxazin-4-ylidene]-2-propanamine

HRID 2052799ノート

反応式

HRID 2052799 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([NH:15][C:16]2[C:21]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:28])=O)=[CH:11][C:10]([C:29]([F:32])([F:31])[F:30])=[N:9]1.S(Cl)(Cl)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[O:23][C:22](=[N:24][CH:25]([CH3:26])[CH3:27])[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:28])[C:16]=3[N:15]=2)=[CH:11][C:10]([C:29]([F:32])([F:31])[F:30])=[N:9]1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 444044961-(2-Chlorophenyl)-n-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1h-pyrazole-5-carboxamide

生成物 1

HCID 69183093n-[2-[1-(2-Chlorophenyl)-3-(trifluoromethyl)-1h-pyrazol-5-yl]-8-methyl-4h-3,1-benzoxazin-4-ylidene]-2-propanamine収率 58%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To the title compound of Step D (1.2 g, 2.7 mmol) dissolved in 8 mL of dichloromethane, 5 mL of thionyl chloride was added and the solution heated at reflux for 8 hours. The solvent was removed in vacuo and remaining residue partitioned between 70 mL of ethyl acetate and water. The organic layer was separated, washed with water, saturated aqueous sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo to give a crude oily solid residue. Purification by flash chromatography on silica gel (2:1 hexane/ethyl acetate) and filtering from hexane afforded 700 mg of the title compound, a compound of the invention, isolated as a white solid melting at 133-135° C.

後処理

  1. temperaturethe solution heated
  2. temperatureat reflux for 8 hours
  3. customThe solvent was removed in vacuo
  4. custompartitioned between 70 mL of ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water, saturated aqueous sodium bicarbonate and brine
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customto give a crude oily solid residue
  10. customPurification by flash chromatography on silica gel (2:1 hexane/ethyl acetate)
  11. filtrationfiltering from hexane

出典と根拠

ORDレコード
ord-16bcc87ccb6b44979d73f623c4ca14f4
出典データセット
uspto-grants-2008_02
特許番号
US07326704B2

反応ノート

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