Water → HCID 68277390, compound

HRID 1048803Notes

Reaction equation

HRID 1048803 reaction equation
[H-].[Na+].[C:3]([N:7]1[C:11]2=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[CH:15]=[C:10]2[C:9]([NH2:25])=[N:8]1)([CH3:6])([CH3:5])[CH3:4].[N:26]([C:29]1[CH:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[CH:31][CH:30]=1)=[C:27]=[O:28].O>CC(N(C)C)=O>[C:3]([N:7]1[C:11]2=[N:12][CH:13]=[C:14]([S:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[CH:15]=[C:10]2[C:9]([NH:25][C:27]([NH:26][C:29]2[CH:30]=[CH:31][C:32]([N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)=[CH:33][CH:34]=2)=[O:28])=[N:8]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 185257091-(4-Isocyanatophenyl)-4-methylpiperazineHCID 68277264HCID 68277264, compound

Product 1

HCID 68277390HCID 68277390, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.048 g (1.19 mmol) of sodium hydride is added at 0° C. to 0.200 g (0.598 mmol) of 1-tert-butyl-5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine dissolved in 10 ml of anhydrous dimethylacetamide. The reaction is left under stirring for 10 minutes. 0.130 g (0.598 mmol) of 1-(4-isocyanatophenyl)-4-methylpiperazine is then added at 0° C. The mixture is left under stirring for 3 hours at room temperature. The reaction is treated by adding 20 ml of water drop by drop at 0° C. and then is extracted with ethyl acetate. The organic phase is dried on sodium sulfate, filtered and concentrated. The product is purified by silica chromatography to yield 0.150 g (yield=45%) of 1-(1-tert-butyl-5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-(4-(4-methylpiperazin-1-yl)phenyl)urea in the form of a light brown solid.

Workup

  1. waitThe reaction is left
  2. waitThe mixture is left
  3. stirringunder stirring for 3 hours at room temperature
  4. additionThe reaction is treated
  5. extractionis extracted with ethyl acetate
  6. customThe organic phase is dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product is purified by silica chromatography

Sources & evidence

ORD record
ord-47c1b251b3f74a4c97fe787aa54928ef
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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