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

HRID 2198155ノート

反応式

HRID 2198155 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a1d432caf464cfd976671b1e59542f1
出典データセット
uspto-grants-2012_12
特許番号
US08338610B2

反応ノート

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