Oxalyl chloride → N'-[3-[3-(trifluoromethyl)phenyl]propionyl]-1H-indazole-5-carbohydrazide

HRID 452594노트

반응식

HRID 452594 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:7][CH:8]=1.C(Cl)(=O)C(Cl)=O.[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([C:31]([NH:33][NH2:34])=[O:32])=[CH:28][CH:29]=2)[CH:24]=[N:23]1.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[F:14][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([NH:34][NH:33][C:31]([C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[NH:22][N:23]=[CH:24]3)=[O:32])=[O:13])[CH:6]=[CH:7][CH:8]=1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 27776833-(3-Trifluoromethylphenyl)propanoic acidHCID 433489731H-Indazole-5-carbohydrazide

생성물 1

HCID 68663677N'-[3-[3-(trifluoromethyl)phenyl]propionyl]-1H-indazole-5-carbohydrazide수율 51%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-[3-(trifluoromethyl)phenyl]propionic acid (437 mg, 2.00 mmol) and N,N-dimethylformamide (1 drop) in tetrahydrofuran (4 mL) was added oxalyl chloride (0.183 mL, 2.10 mmol) at room temperature, and the resulting mixture was stirred for 30 min. The reaction mixture was added dropwise to a mixture of 1H-indazole-5-carbohydrazide (352 mg, 2.00 mmol), tetrahydrofuran (10 mL) and saturated aqueous sodium hydrogen carbonate solution (10 mL) at room temperature, and the resulting mixture was stirred for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethanol to give the title compound (383 mg, yield 51%) as colorless crystals.

후처리

  1. stirringthe resulting mixture was stirred for 2 hr
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethanol

출처 및 근거

ORD 기록
ord-69f4f92427c74619a90092a49b028bc5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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