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

HRID 559686Notes

Reaction equation

HRID 559686 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4d99dc6a43b942a2bc5f18d9655dbeff
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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