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Potassium Carbonate → 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224244
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HRID 2224244 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[NH:15][N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:40])[F:39])=[N:36][CH:37]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][N:11]3[C:14](=[O:17])[N:15]([CH2:31][C:32]4[CH:37]=[N:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][CH:33]=4)[N:16]=[C:10]3[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 597167437-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

생성물 1

HCID 119897617-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one수율 76.1%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
65 °C

실험 절차

A solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (1.1 g, 3.4 mmol), prepared as described in Example 244, K2CO3 (940 mg, 6.8 mmol), and 5-chloromethyl-2-trifluoromethylpyridine (800 mg, 4.1 mmol) in DMF (8.3 mL) was heated at 65° C. for 40 min. After this time, the solution was cooled to RT The reaction mixture was partitioned between water and EtOAc. The organic layer separated, washed with water and saturated aqueous NaCl. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with hexanes/EtOAc to give the title compound, 7-(4-chlorophenyl)-8-(pyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (1.25 g, 76%) as a yellow solid. HPLC: 2.84 min; MS, M+H=483; 1H NMR (CDCl3) δ 8.80 (d, J=1.4 Hz, 1H), 8.65 (Abq, J=1.6, 4.4 Hz, 2H), 8.23 (s, 1H), 7.96 (m, 1H), 7.68 (d, J=8.3 Hz, 1H), 7.34 (m, 2H), 7.23 (m, 2H), 7.10 (m, 2H), 5.31 (2H).

후처리

  1. temperatureAfter this time, the solution was cooled to RT The reaction mixture
  2. customwas partitioned between water and EtOAc
  3. customThe organic layer separated
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with hexanes/EtOAc

출처 및 근거

ORD 기록
ord-bfe5866fcaab4a26876bdd9e4535f002
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378418B2

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