Water → HCID 86655381, 화합물

HRID 2190432노트

반응식

HRID 2190432 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O:34][CH2:35][C:36](Cl)=[O:37])(=O)C.O>CN(C)C=O>[C:35]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=3)[C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=3)=[O:16])[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:34])[CH2:36][OH:37]

참가 물질

5

반응물 3

HCID 962WaterHCID 26297Acetoxyacetyl chlorideHCID 86655379HCID 86655379, 화합물

생성물 1

HCID 86655381HCID 86655381, 화합물수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-N-[3-(trifluoromethyl)phenyl]benzamide (429 mg, 1.0 mmol) produced in Example A29(v) and 2-chloro-2-oxoethyl acetate (546 mg, 4.0 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 6 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (300 mg, 62%) as a pale-yellow solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (5 mL)/tetrahydrofuran (5 mL), 8N aqueous sodium hydroxide solution (1 mL)
  5. additionwas added under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred at room temperature for 30 min
  8. additionThe reaction mixture was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  13. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-5c405e6239dc499792d386354385aa36
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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