Water → HCID 86655382, 화합물

HRID 2190433노트

반응식

HRID 2190433 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.Cl[CH2:32][C:33](Cl)=[O:34].O.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C)C=O>[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([CH2:32][C:33]([NH:1][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:11][C:12]4[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=4)[C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=4)=[O:16])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[O:34])[CH2:40][CH2:39]1

참가 물질

6

반응물 4

HCID 962Water2회HCID 6577Chloroacetyl chlorideHCID 531671-MethylpiperazineHCID 86655379HCID 86655379, 화합물

생성물 1

HCID 86655382HCID 86655382, 화합물수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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 chloroacetyl chloride (225 mg, 2.0 mmol) in N,N-dimethylformamide (10 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, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1) to give a colorless oil. This was dissolved in N,N-dimethylformamide (5 mL), 1-methylpiperazine (400 mg, 4.0 mmol) was added, and the mixture was stirred at room temperature for 1 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 purified by basic silica gel chromatography (eluent:ethyl acetate/methanol=10:1), and triturated with diethyl ether to give the title compound (340 mg, 60%) as a white 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. customthe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1:1)
  5. customto give a colorless oil
  6. stirringthe mixture was stirred at room temperature for 1 hr
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by basic silica gel chromatography (eluent:ethyl acetate/methanol=10:1)
  11. customtriturated with diethyl ether

출처 및 근거

ORD 기록
ord-f10513f9170145eaa4521e45d26321c0
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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