Methyl isothiocyanate → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (5-methylamino-1,3,4-thiadiazol-2-ylmethyl)-amide

HRID 1698185노트

반응식

HRID 1698185 반응식
[NH:1]([C:3]([CH2:5][NH:6][C:7]([C:9]1[C:10]2[CH:17]=[N:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:11]=2[CH:12]=[N:13][CH:14]=1)=[O:8])=O)[NH2:2].[CH3:25][N:26]=[C:27]=[S:28]>CCO>[CH3:25][NH:26][C:27]1[S:28][C:3]([CH2:5][NH:6][C:7]([C:9]2[C:10]3[CH:17]=[N:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C:11]=3[CH:12]=[N:13][CH:14]=2)=[O:8])=[N:1][N:2]=1

참가 물질

4

반응물 2

HCID 11167Methyl isothiocyanateHCID 667277641-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid hydrazinocarbonylmethyl-amide

생성물 1

HCID 592784091-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (5-methylamino-1,3,4-thiadiazol-2-ylmethyl)-amide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a mixture of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid hydrazinocarbonylmethyl-amide (104 mg, 0.32 mmol) in EtOH (4 mL) was added methyl isothiocyanate (50 mg, 0.7 mmol). The mixture was warmed at reflux for 6 days, and was then cooled to room temperature, and the product was collected by filtration. The crude material was suspended in concentrated sulfuric acid (1 mL) and stirred for 10 minutes. After standing for 10 minutes, the mixture was poured into ice water. The solution was made basic by addition of aqueous ammonia followed by a minimal amount of saturated aqueous sodium bicarbonate to pH=8 and the solid collected by filtration to afford title compound.

후처리

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 6 days
  3. filtrationthe product was collected by filtration
  4. waitAfter standing for 10 minutes
  5. additionthe mixture was poured into ice water
  6. additionThe solution was made basic by addition of aqueous ammonia
  7. filtrationthe solid collected by filtration

출처 및 근거

ORD 기록
ord-435f88fdb873470691137dd1cf9660a0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163918B2

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