Water → N-(3-{[2-(hydroxymethyl)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1667887

反応式

HRID 1667887 の反応式
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[N:7]=1.[OH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]([C:23]2[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[OH:12][CH2:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:7][N:6]2[CH:8]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19481482N-(3-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamideHCID 57441048(6-Iodoimidazo[1,2-b]pyridazin-2-yl)methanol

生成物 1

HCID 57505461N-(3-{[2-(hydroxymethyl)imidazo[1,2-b]pyridazin-6-yl]oxy}phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 13%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To a solution of (6-iodoimidazo[1,2-b]pyridazin-2-yl)methanol (400 mg, 1.45 mmol) in N,N-dimethylformamide (4.0 mL) were added N-(3-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (504 mg, 2.18 mmol) and potassium carbonate (402 mg, 2.91 mmol), and the mixture was stirred at 150° C. for 16 hr. After cooling the mixture to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/ethanol=100/0→10/1) to give the title compound (70 mg, 13%) as a white powder.

後処理

  1. temperatureAfter cooling the mixture to room temperature
  2. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/ethanol=100/0→10/1)

出典と根拠

ORDレコード
ord-def0a9d79033427d9da5cbc9359dfa4b
出典データセット
uspto-grants-2011_10
特許番号
US08044049B2

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