Pipemidic Acid → HCID 22760702, compound

HRID 1703792Notes

Reaction equation

HRID 1703792 reaction equation
[N:1]1([C:7]2[N:8]=[CH:9][C:10]3[C:16](=[O:17])[C:15]([C:18]([OH:20])=[O:19])=[CH:14][N:13]([CH2:21][CH3:22])[C:11]=3[N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:29]([NH:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)(=[O:31])[CH3:30]>CN(C)C=O.O>[C:29]([NH:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[N:8]=[CH:9][C:10]4[C:16](=[O:17])[C:15]([C:18]([OH:20])=[O:19])=[CH:14][N:13]([CH2:21][CH3:22])[C:11]=4[N:12]=3)[CH2:6][CH2:5]2)=[CH:35][CH:34]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 4831Pipemidic AcidHCID 11430Potassium CarbonateHCID 149290Acetamide, N-(4-(bromomethyl)phenyl)-

Product 1

HCID 22760702HCID 22760702, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 35.3 g of 2-(1-piperazinyl)-8-ethyl-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid in 500 ml of dimethylformamide was added a solution of 39.0 g of potassium carbonate in 50 ml of water and then 39.5 g of p-acetamidobenzyl bromide. The mixture was heated at 80°-90° C. for 1.5 hours with stirring. After removal of a small amount of the insoluble material by filtration, the filtrate was concentrated to dryness under reduced pressure and the residue was dissolved in 100 ml of water. The solution was adjusted to pH 7.0 with acetic acid. The precipitate was collected by filtration and recrystallized from a mixture of dimethylformamide and ethanol to give the product (42.3 g), m.p. 216.5°-219° C.

Workup

  1. temperatureThe mixture was heated at 80°-90° C. for 1.5 hours
  2. customAfter removal of a small amount of the insoluble material
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. dissolutionthe residue was dissolved in 100 ml of water
  6. filtrationThe precipitate was collected by filtration
  7. customrecrystallized from a mixture of dimethylformamide and ethanol

Sources & evidence

ORD record
ord-a212cb41d2154ec3a29fdf56e69e5e7b
Source dataset
uspto-grants-1978_11
Patent number
US04125615

Reaction notes

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