Dimethylformamide → HCID 15158097, compound

HRID 1084850Notes

Reaction equation

HRID 1084850 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][CH:9]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:23][N:22]=2)=[CH:17][CH:16]=1)[CH2:10][N:11]([CH3:13])[CH3:12].Cl[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>C1(C)C=CC=CC=1.O>[CH3:8][CH:9]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[N:22]=2)=[CH:17][CH:16]=1)[CH2:10][N:11]([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 178457413HCID 178457413, compound

Product 1

HCID 15158097HCID 15158097, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

In 40 ml of toluene was suspended 2.3 g of 60% sodium hydride, and 40 ml of dimethylformamide was added to the suspension under ice-cooling. Thereto was added in the two or three times divided manner 14.8 g of 3-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine. After the mixture was stirred for 15 minutes, a solution of 7.0 g of ethyl chloroacetate in 70 ml of toluene was added dropwise. The mixture was stirred at room temperature for 1 hour, and then it was stirred at 40° C. for 1 hour. After cooling, water was added. The toluene layer was separated, washed with water and dried. Toluene was distilled off. The residue was purified by chromatography to give ethyl 3-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-1H-pyrazolo[3,4-b]-pyridin-1-ylacetate in an oily form.

Workup

  1. additionwas added to the suspension under ice-
  2. temperaturecooling
  3. additionThereto was added in the two or three times
  4. stirringThe mixture was stirred at room temperature for 1 hour
  5. stirringit was stirred at 40° C. for 1 hour
  6. temperatureAfter cooling
  7. customThe toluene layer was separated
  8. washwashed with water
  9. customdried
  10. distillationToluene was distilled off
  11. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-0bcb0a028cca4e4f8d65d8d59a759914
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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