Acetic Acid → 2-{1-[1-(Diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}-4-fluorophenol

HRID 46353노트

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HRID 46353 반응식
Cl.Cl.[C:3]1([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]2[CH2:13][CH:12]([NH:14][NH2:15])[CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.CN(C)/[CH:28]=[CH:29]/[C:30]([C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[OH:39])=O>C(O)C>[C:16]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:10]2[CH2:13][CH:12]([N:14]3[C:30]([C:32]4[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=4[OH:39])=[CH:29][CH:28]=[N:15]3)[CH2:11]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 5713860(2E)-3-(dimethylamino)-1-(5-fluoro-2-hydroxyphenyl)prop-2-en-1-oneHCID 601459041-Benzhydryl-3-hydrazinylazetidine dihydrochloride

생성물 1

HCID 1360636272-{1-[1-(Diphenylmethyl)azetidin-3-yl]-1H-pyrazol-5-yl}-4-fluorophenol

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

1-(diphenylmethyl)-3-hydrazinoazetidine dihydrochloride (Preparation 690, 1.25 g, 4.30 mmol) was stirred in ethanol (20 ml) and acetic acid (8 ml) for 30 minutes with ice cooling to give a suspension. To this cold suspension was added (2E)-3-(dimethylamino)-1-(5-fluoro-2-hydroxyphenyl)prop-2-en-1-one (Preparation 221, 900 mg, 4.3 mmol), stirred at 0° C. for 1 hour then allowed to warm up to room temperature over 18 hours. The reaction mixture was evaporated and then partitioned between ethyl acetate (100 ml), water (50 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml). The organic layer was separated and back-washed with saturated aqueous sodium chloride solution (2×20 ml), dried over sodium sulphate, filtered and evaporated. The solid was triturated with diethyl ether and the off-white solid filtered. The solid was crystallized from ethyl acetate:hexane (1:4) to give the title compound as colourless crystals were. Yield 490 mg 29%.

후처리

  1. temperatureto warm up to room temperature over 18 hours
  2. customThe reaction mixture was evaporated
  3. custompartitioned between ethyl acetate (100 ml), water (50 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml)
  4. customThe organic layer was separated
  5. washback-washed with saturated aqueous sodium chloride solution (2×20 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe solid was triturated with diethyl ether
  10. filtrationthe off-white solid filtered
  11. customThe solid was crystallized from ethyl acetate:hexane (1:4)

출처 및 근거

ORD 기록
ord-0050c3ac8bcc40f689df6ccbd8d9a1db
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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