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

반응식

HRID 1874513 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a4ece0ed46dd4d0eabb5c4763283bfda
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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