Water → 3,8-diphenyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrido[2,3-d]pyridazine

HRID 1357472ノート

反応式

HRID 1357472 の反応式
[C:1]1([C:7]2[C:22](=[O:23])[NH:21][C:10]3=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:12]=[N:13][CH:14]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:31][C:32]1[N:33]([CH3:37])[N:34]=[CH:35][N:36]=1.O>CN(C=O)C>[C:1]1([C:7]2[C:22]([O:23][CH2:31][C:32]3[N:33]([CH3:37])[N:34]=[CH:35][N:36]=3)=[N:21][C:10]3=[C:11]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:12]=[N:13][CH:14]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 104192195-(Chloromethyl)-1-methyl-1H-1,2,4-triazoleHCID 114834053,8-diphenyl-1H-pyrido[2,3-d]pyridazin-2-one

生成物 1

HCID 99525193,8-diphenyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrido[2,3-d]pyridazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3,8-Diphenyl-1H-pyrido[2,3-d]pyridazin-2-one (40 mg), cesium carbonate (174 mg) and 3-(chloromethyl)-2-methyl-2H-[1,2,4]triazole (prepared using the conditions described in EP-A-0170073) (27 mg) were stirred together at room temperature in DMF (4 ml) under nitrogen overnight. Water (25 ml) was added and the resultant solution was washed with dichloromethane (3×25 ml). The combined organic washings were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel, eluting with 5% methanol in dichloromethane. The product was recrystallised froim diethyl ether/ethanol/ethyl acetate, yielding 3,8-diphenyl-2-(2-methyl-2H-[1,2,4]triazol-3-ylmethoxy)pyrido[2,3-d]pyridazine as a white solid (8 mg). Data for the title compound: m.p. 222-223° C. 1H NMR (400 MHz, CDCl3) δ3.62 (3H, s), 5.67 (2H, s), 7.48 (3H, m), 7.56 (3H, m), 7.63 (2H, m), 7.85 (1H, s), 8.13 (2H, m), 8.20 (1H, s), 9.49 (1H, s); MS (ES+) m/e 395 [MH]+.

後処理

  1. washthe resultant solution was washed with dichloromethane (3×25 ml)
  2. dry with materialThe combined organic washings were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography on silica gel
  5. washeluting with 5% methanol in dichloromethane
  6. customThe product was recrystallised froim diethyl ether/ethanol/ethyl acetate

出典と根拠

ORDレコード
ord-ad768ea6a5f7458fa311874e6b74231f
出典データセット
uspto-grants-2003_07
特許番号
US06593325B1

反応ノート

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