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6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine → 6-[4-(5-Bromopyridin-2-yl)piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674775
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HRID 1674775 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl[C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][N:23]=2)[N:20]=1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([C:21]([C:24]([F:25])([F:27])[F:26])=[N:22][N:23]=4)[N:20]=3)[CH2:12][CH2:13]2)=[N:6][CH:7]=1
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참가 물질

4

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HCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 164142271-(5-Bromopyridin-2-yl)piperazine

생성물 1

HCID 368336896-[4-(5-Bromopyridin-2-yl)piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine수율 73.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

A mixture of 1-(5-bromopyridin-2-yl)piperazine and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine in ethanol (7 mL) was stirred at 80° C. for 20 hours. The reaction mixture was concentrated and partitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (25 mL). The aqueous phase was extracted twice with dichloromethane (2×50 mL). The organic phases were combined, washed with water (100 mL), and concentrated to give a residue that was purified by flash chromatography on silica-gel using ethyl acetate as eluant to give 6-[4-(5-bromopyridin-2-yl)piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine 0.353 g, 73.4%)

후처리

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between dichloromethane (50 mL) and saturated aqueous sodium bicarbonate solution (25 mL)
  3. extractionThe aqueous phase was extracted twice with dichloromethane (2×50 mL)
  4. washwashed with water (100 mL)
  5. concentrationconcentrated
  6. customto give a residue that
  7. customwas purified by flash chromatography on silica-gel

출처 및 근거

ORD 기록
ord-d6860edd11ed4533ba150f0c21bbc8e4
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08003649B2

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