Benzylhydrazine dihydrochloride → 1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazole

HRID 591076노트

반응식

HRID 591076 반응식
Cl.Cl.[CH2:3]([NH:10][NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:12]1[C:17]2[CH:18]=[CH:19][C:20]([C:22](=O)[CH2:23][C:24](=O)[C:25]([F:28])([F:27])[F:26])=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13]1>C(#N)C>[CH2:3]([N:10]1[C:22]([C:20]2[CH:19]=[CH:18][C:17]3[O:12][CH2:13][CH2:14][CH2:15][C:16]=3[CH:21]=2)=[CH:23][C:24]([C:25]([F:28])([F:26])[F:27])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 146540Benzylhydrazine dihydrochlorideHCID 708188081-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,4-trifluorobutane-1,3-dione

생성물 1

HCID 708554551-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazole수율 39.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of benzylhydrazine dihydrochloride (394 mg, 2.03 mmol) and 1-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,4-trifluorobutane-1,3-dione (49b) (500 mg, 1.84 mmol) in acetonitrile (80 mL) was refluxed for 16 hours. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate (5 mL). The organic layer was successively washed with water (10 mL) and brine (10 mL) before being dried over sodium sulfate and concentrated in vacuo. The oil was purified by preparative TLC (cyclohexane/ethyl acetate 100/0 to 90/10) to provide the desired pyrazole (49c) (260 mg, 0.73 mmol, 39%).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. washThe organic layer was successively washed with water (10 mL) and brine (10 mL)
  3. dry with materialbefore being dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oil was purified by preparative TLC (cyclohexane/ethyl acetate 100/0 to 90/10)

출처 및 근거

ORD 기록
ord-29eb6989148f4e43b5766646a4e9aa1c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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