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

HRID 132512노트

반응식

HRID 132512 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
0 °C

실험 절차

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.).

후처리

  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.)

출처 및 근거

ORD 기록
ord-a293b8acbc0e4d598af51218e26f2e43
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388006B2

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