Acetyl chloride → 1-Propanol,3-[(5-methyl-1h-pyrazolo[4,3-b]pyridin-7-yl)amino]-,1-acetate

HRID 620019Notes

Reaction equation

HRID 620019 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12.[C:16](Cl)(=[O:18])[CH3:17].[OH-].[Na+]>O>[C:16]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 137471677-[3-hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 212483751-Propanol,3-[(5-methyl-1h-pyrazolo[4,3-b]pyridin-7-yl)amino]-,1-acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 7(3-hydroxypropylamino)-5-methyl-1H-pyrazolo[4,3-b]pyridine (1.125 g) and acetyl chloride by the general method of Example 4 with the following addition. After removal of solvents under reduced pressure the crude reaction mixture was dissolved in water and brought to pH 9 with 10% sodium hydroxide. The resulting solid was collected and dried before purifying by column chromatography under the conditions used for Example 4. A clear gum was obtained which on trituration with ether gave the title compound as a white solid, m.p. 115°-119° C.

Workup

  1. customAfter removal of solvents under reduced pressure the crude
  2. customreaction mixture
  3. customThe resulting solid was collected
  4. customdried
  5. custombefore purifying by column chromatography under the conditions
  6. customA clear gum was obtained which on trituration with ether

Sources & evidence

ORD record
ord-611a4ea366eb4bd18f5895c37ed0651c
Source dataset
uspto-grants-1989_04
Patent number
US04818754

Reaction notes

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