Sodium hydride → 7-(1,1-Dimethylethyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-1,2,4-triazolo(4,3-b)pyridazine

HRID 986914ノート

反応式

HRID 986914 の反応式
[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[N:6][CH:5]=[N:4]1)[CH3:2].Cl[C:11]1[C:12]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:13][C:14]2[N:15]([C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[N:18][N:19]=2)[N:16]=1.[H-].[Na+]>CN(C=O)C.O>[CH3:30][C:27]([C:12]1[C:11]([O:9][CH2:8][C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][N:6]=2)=[N:16][N:15]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[N:18][N:19]=[C:14]2[CH:13]=1)([CH3:28])[CH3:29]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 111508847-Tert-butyl-6-chloro-3-(2-fluorophenyl)-[1,2,4]triazolo[4,3-b]pyridazineHCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanol

生成物 1

HCID 99086847-(1,1-Dimethylethyl)-6-((1-ethyl-1H-1,2,4-triazol-5-yl)methoxy)-3-(2-fluorophenyl)-1,2,4-triazolo(4,3-b)pyridazine収率 44%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (2-ethyl-2H-1,2,4-triazol-3-yl)methanol (0.094 g, 0.74 mmol) and 6-chloro-7-(1,1-dimethylethyl)-3-(2-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine (0.15 g. 0.49 mmol) in DMF (10 ml) was added sodium hydride (0.024 g of a 60% dispersion in oil, 1.1 mol eq.) and the reaction mixture was stirred at room temperature for 30 minutes. After this time, the reaction mixture was diluted with water (80 ml) and the solid that precipitated was collected by filtration and washed several times with water in the sinter funnel. The solid was recrystallised from ethyl acetate/hexane to give pure title compound (0.085 g, 44%). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ1.40-1.47 (12H, m), 4.14 (2H, t, J=7.3 Hz), 5.26 (2H, s), 7.26-7.38 (2H, m), 7.53-7.58 (1H, m), 7.86-7.90 (1H, m), 7.93 (1H, s), 7.99 (1H, s); MS (ES+) m/e 396 [MH]+. Anal. Found C, 61.02; H, 5.45; N, 24.75%. C20H22FN7O requires C, 60.75; H, 5.61; N, 24.79%.

後処理

  1. customthe solid that precipitated
  2. filtrationwas collected by filtration
  3. washwashed several times with water in the sinter funnel
  4. customThe solid was recrystallised from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-4eb6d2d7b25b4525bfc187de130b2887
出典データセット
uspto-grants-2003_10
特許番号
US06630471B1

反応ノート

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