Water → (4-Hydroxy-3-trifluoromethyl-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone
반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(Cl)(Cl)=O.C[N:20]1[CH:25]2[O:26][CH2:27][CH2:28][NH:29][C:24]2=[CH:23][CH:22]=[CH:21]1.O.[CH3:31]N(C)C(=O)C>>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:29]2[CH2:28][CH2:27][O:26][C:25]3[N:20]=[CH:21][C:22]([CH3:31])=[CH:23][C:24]2=3)=[O:8])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]참가 물질
반응물 5
생성물 1
반응 조건
- 온도
- -20 °C
실험 절차
4-hydroxy-3-trifluoromethyl-benzoic acid (151 mg, 0.73 mmol) was dissolved in N,N-dimethyl acetamide (2.0 ml) and then cooled to −20° C. Thionyl chloride (0.073 ml, 100 mmol) was added thereto and stirred at −20° C. for 30 minutes. 5-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine dissolved in N,N-dimethyl acetamide (1.0 ml) was added thereto dropwise and then stirred at −20° C. for 20 minutes, and then stirred at room temperature for 15 hours. Water was added thereto and the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting solid residue was recrystallized from dichloromethane to obtain the target compound 69, i.e., (4-hydroxy-3-trifluoromethyl-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone, as white solid (176 mg, 78%).
후처리
- additionwas added
- stirringdropwise and then stirred at −20° C. for 20 minutes
- stirringstirred at room temperature for 15 hours
- extractionthe mixture was extracted with dichloromethane
- dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
- filtrationfiltered
- customevaporated under reduced pressure
- customThe resulting solid residue was recrystallized from dichloromethane
출처 및 근거
- ORD 기록
- ord-c3cbd4800d9746ce9e0ad489328da1e1
- 출처 데이터셋
- uspto-grants-2013_03
- 특허 번호
- US08394792B2
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