Dimethylformamide → HCID 14796402, compound

HRID 1084849Notes

Reaction equation

HRID 1084849 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][N:14]=2)=[CH:9][CH:8]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]>O>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:35][C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])[N:14]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 11430Potassium CarbonateHCID 178483568HCID 178483568, compound

Product 1

HCID 14796402HCID 14796402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 9 g of 3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridine, 30 ml of dimethylformamide and 6.2 g of potassium carbonate was added dropwise 6.6 g of benzyl chloroacetate at 50° C. over the period of 2 hours. The mixture was kept at the same temperature for 4 hours. After the completion of the reaction, the reaction mixture was cooled. Water was added thereto, and the mixture was extracted with toluene. The extract was washed with water. After toluene was distilled off, diisopropyl ether was added to the residue for crystallization. The resulting crystals were recrystallized from diisopropyl ether - ethyl acetate to give benzyl 3-[4-(3-dimethylaminopropoxy)phenyl]-1H-pyrazolo[3,4-b]pyridin-1-ylacetate, m.p. 90°-92° C.

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. extractionthe mixture was extracted with toluene
  4. washThe extract was washed with water
  5. distillationAfter toluene was distilled off
  6. additiondiisopropyl ether was added to the residue for crystallization
  7. customThe resulting crystals were recrystallized from diisopropyl ether - ethyl acetate

Sources & evidence

ORD record
ord-21ebf5f8bff3437da3f74bfabf5a4449
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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