1-Benzhydryl-3-hydrazinylazetidine hydrochloride → 1-(1-benzhydrylazetidin-3-yl)-5-(2-bromo-5-(trifluoromethyl)phenyl)-1H-pyrazole

HRID 1473343노트

반응식

HRID 1473343 반응식
Cl.[CH:2]([N:15]1[CH2:18][CH:17]([NH:19][NH2:20])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=1[C:32](=O)/[CH:33]=[CH:34]/N(C)C>C(O)C.C(O)(=O)C>[CH:2]([N:15]1[CH2:16][CH:17]([N:19]2[C:32]([C:23]3[CH:24]=[C:25]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:27][C:22]=3[Br:21])=[CH:33][CH:34]=[N:20]2)[CH2:18]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 866873901-Benzhydryl-3-hydrazinylazetidine hydrochlorideHCID 86687392(E)-1-(2-bromo-5-(trifluoromethyl)phenyl)-3-(dimethylamino)prop-2-en-1-one

생성물 1

HCID 866873911-(1-benzhydrylazetidin-3-yl)-5-(2-bromo-5-(trifluoromethyl)phenyl)-1H-pyrazole수율 39.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

To a solution of compound 1-benzhydryl-3-hydrazinylazetidine hydrochloride (15.5 g, 49.6 mmol) in ethanol (150 mL), a mixture of (E)-1-(2-bromo-5-(trifluoromethyl)phenyl)-3-(dimethylamino)prop-2-en-1-one (16 g, 49.6 mmol) in acetic acid (15 mL) was added slowly at 0° C. The reaction was stirred at the same temperature for 8 h. After warming to rt, the solvent was completely evaporated off. The residue was diluted with ethyl acetate (500 mL), washed with water (500 mL), and saturated aqueous sodium bicarbonate (30 mL). Organic part was dried over sodium sulfate, filtered and concentrated under a vacuum to give the crude which was further purified by column chromatography using silica gel (100 to 200 mesh) eluting with 0% to 10% ethyl acetate in hexanes to obtain 1-(1-benzhydrylazetidin-3-yl)-5-(2-bromo-5-(trifluoromethyl)phenyl)-1H-pyrazole (10 g, 39.3%) as a sticky yellow solid. MS (ESI, positive ion) m/z (M+1): 512.01. 1H NMR (400 MHz, DMSO) δ 8.03 (d, J=8.3 Hz, 1H), 7.80 (d, J=8.5 Hz, 1H), 7.77 (s, 1H), 7.68 (d, J=1.5 Hz, 1H), 7.43 (d, J=7.4 Hz, 4H), 7.26 (t, J=7.5 Hz, 4H), 7.17 (t, J=7.3 Hz, 2H), 6.41 (d, J=1.5 Hz, 1H), 4.66-4.59 (m, 1H), 4.57 (s, 1H), 3.46 (dt, J=26.3, 7.3 Hz, 4H).

후처리

  1. additionwas added slowly at 0° C
  2. customthe solvent was completely evaporated off
  3. additionThe residue was diluted with ethyl acetate (500 mL)
  4. washwashed with water (500 mL), and saturated aqueous sodium bicarbonate (30 mL)
  5. dry with materialOrganic part was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under a vacuum
  8. customto give the crude which
  9. customwas further purified by column chromatography
  10. washeluting with 0% to 10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-209a89648d1f4b94afcb0b7f5d2f4047
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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