Water → N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874513

反応式

HRID 1874513 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16]([C:18]3[N:22]([CH3:23])[N:21]=[C:20]([CH3:24])[CH:19]=3)=[O:17])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[S-:25][C:26]#[N:27].[K+].BrBr.O>C(O)(=O)C>[NH2:27][C:26]1[S:25][C:7]2[C:2]([N:1]=1)=[CH:3][CH:4]=[C:5]([O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]([C:18]3[N:22]([CH3:23])[N:21]=[C:20]([CH3:24])[CH:19]=3)=[O:17])[CH:12]=[CH:13][CH:14]=1)[N:6]=2

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 516872Potassium thiocyanateHCID 57749235N-{3-[(5-aminopyridin-2-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 57749158N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide収率 51%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
80 °C

実験手順

To a suspension of N-{3-[(5-aminopyridin-2-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (1.75 g, 5.41 mmol) and potassium thiocyanate (4.21 g, 43.3 mmol) in acetic acid (10 mL) was added dropwise with stirring under ice-cooling a solution of bromine (1 mL) in acetic acid (4 mL), and the mixture was stirred at 0° C. for 2 hr and at room temperature for 15 hr. Water (10 mL) was added to the reaction mixture, and the mixture was heated to 80° C. and filtered through celite. The filtrate was neutralized with 8N aqueous sodium hydroxide solution, and the precipitated solid was collected by filtration and washed with water to give the title compound (1.05 g, 51%) as a white solid.

後処理

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at 0° C. for 2 hr and at room temperature for 15 hr
  3. filtrationfiltered through celite
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water

出典と根拠

ORDレコード
ord-a4ece0ed46dd4d0eabb5c4763283bfda
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

関連ノート

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