Thionyl Chloride → 6-{3-[1-(3-Trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-4-methyl-2,3-benzoxazin-1-one

HRID 132512ノート

反応式

HRID 132512 の反応式
S(Cl)(Cl)=O.[F:5][C:6]([F:23])([F:22])[C:7]1[CH:8]=[C:9]([C:13]2([CH2:16][C:17](=[O:21])[C:18]([OH:20])=O)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.[NH2:24][C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[O:34])[O:32][N:31]=[C:30]([CH3:35])[C:29]=2[CH:36]=1>CC(N(C)C)=O>[F:22][C:6]([F:5])([F:23])[C:7]1[CH:8]=[C:9]([C:13]2([CH2:16][C:17](=[O:21])[C:18]([NH:24][C:25]3[CH:26]=[CH:27][C:28]4[C:33](=[O:34])[O:32][N:31]=[C:30]([CH3:35])[C:29]=4[CH:36]=3)=[O:20])[CH2:14][CH2:15]2)[CH:10]=[CH:11][CH:12]=1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 111829366-amino-4-methyl-1H-2,3-benzoxazin-1-oneHCID 693039543-[1-(3-Trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionic acid

生成物 1

HCID 693036056-{3-[1-(3-Trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-4-methyl-2,3-benzoxazin-1-one

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
0 °C

実験手順

1.8 ml Thionylchloride are added at −10° C. to 6.0 g of 3-[1-(3-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionic acid (prepared as described in WO 98/54159) in 60 ml of dimethyl acetamide. The mixture is stirred for 30 min. at −10° C. and for 1 hour at 0° C. and then admixed to 5 g of 6-amino-4-methyl-2,3-benzoxazin-1-one. After 16 hours at ambient temperature, the phases are separated between water and ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated. After chromatography on silica gel using hexane and ethyl acetate (10-20%) as a liquid phase, 6.78 g of 6-{3-[1-(3-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-4-methyl-2,3-benzoxazin-1-one are obtained (m.p. 136-139° C.).

後処理

  1. waitAfter 16 hours at ambient temperature
  2. customthe phases are separated between water and ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customare obtained (m.p. 136-139° C.)

出典と根拠

ORDレコード
ord-a293b8acbc0e4d598af51218e26f2e43
出典データセット
uspto-grants-2008_06
特許番号
US07388006B2

反応ノート

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