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Phenol → 4-(Trifluoromethyl)benzyl-7-(4-chloro-phenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

HRID 2224275
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HRID 2224275 반응식
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:24](=[O:25])[N:11]3[N:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15](Cl)[C:10]3=[N:9]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]1([OH:42])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C=O)C.[OH-].[Na+]>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:24](=[O:25])[N:11]3[N:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15]([O:42][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:10]3=[N:9]2)=[CH:5][CH:4]=1
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참가 물질

6

반응물 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 597166974-(Trifluoromethyl)benzyl-8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

생성물 1

HCID 597168494-(Trifluoromethyl)benzyl-7-(4-chloro-phenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 14798
Sodium Hydroxide
용매

실험 절차

To a solution of 2-(4-(trifluoromethyl)benzyl-8-chloro-7-(4-chlorophenyl)-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (16.5 mg, 0.376 mmol) prepared as described in Example 359, in 0.3 mL of DMF at RT, potassium carbonate (19.4 mg, 0.14 mmol) was added followed by phenol (13.2 mg, 0.14 mmol). The mixture was stirred for 4 h. After this time, the reaction mixture was diluted with 5 mL of 1N aqueous sodium hydroxide. The precipitate was collected by filtration and washed with 1N aqueous NaOH, and water. The solid was dried to the title compound, 2-(4-(trifluoromethyl)benzyl-7-(4-chlorophenyl)-8-phenoxy-2H-[1,2,4]triazolo[4,3-b]pyridazin-3-one (15.8 mg) as light yellow solid. HPLC RT: 4.02 min; MS, M+H=497; 1H NMR (CDCl3): δ 8.21 (s, 1H), 7.52-6.97 (m, 13H), 5.12 (s, 2H).

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 1N aqueous NaOH, and water
  3. dry with materialThe solid was dried to the title compound

출처 및 근거

ORD 기록
ord-cb7c2eebb9af422ea148b10a2c6ca92e
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07378418B2

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