Sodium Hydroxide → 7-(3-Benzyloxy-cyclobutyl)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazin-6-one

HRID 2306607노트

반응식

HRID 2306607 반응식
[OH-:1].[Na+].[CH2:3]([O:10][CH:11]1[CH2:14][CH:13]([C:15]2[C:20](Cl)=[N:19][N:18]3[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])=[N:23][N:24]=[C:17]3[CH:16]=2)[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCOCC1.O>[CH2:3]([O:10][CH:11]1[CH2:14][CH:13]([C:15]2[C:20](=[O:1])[NH:19][N:18]3[C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])=[N:23][N:24]=[C:17]3[CH:16]=2)[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 226099487-(3-Benzyloxycyclobutyl)-6-chloro-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine

생성물 1

HCID 226099297-(3-Benzyloxy-cyclobutyl)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazin-6-one

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

4N Sodium hydroxide (3 ml, 12 mmol) was added to a solution of 7-(3-benzyloxycyclobutyl)-6-chloro-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine (0.98 g, 2.4 mmol) in 1,4-dioxane (30 ml) and water (8 ml), heated to reflux for 18 hours. The solvent was evaporated and the residue dissolved in diethyl ether (50 ml) and water (50 ml) and separated. The aqueous layer was acidified to pH 2 with 2N hydrochloric acid and the resultant solid collected by filtration, washed with water (50 ml), followed by diethyl ether (50 ml) and dried under vacuum at 100° C. for 18 hours. Data for the title compound: 1H NMR (400 MHz, CDCl3), cis and trans isomers present in 4:1 ratio, δ 1.95-2.03 (1.6H, m), 2.31-2.38 (0.4H, m), 2.50-2.56 (0.4H, m), 2.68-2.76 (1.6, m), 3.05-3.13 (1H, m), 3.65-3.73 (0.2H, m), 4.06-4.15 (0.8H, m), 4.46 (2H, s), 6.80-6.87 (2H, m), 7.22-7.37 (6H, m), 7.55-7.61 (1H, m), 7.63 (0.8H, m), 7.68 (0.2H, s); MS (ES+) m/e 391 [MH]+.

후처리

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in diethyl ether (50 ml)
  5. customwater (50 ml) and separated
  6. filtrationthe resultant solid collected by filtration
  7. washwashed with water (50 ml)
  8. customdried under vacuum at 100° C. for 18 hours

출처 및 근거

ORD 기록
ord-0f8c675369f4430796b7f6215978e3ff
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06828322B2

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