Pipemidic Acid → HCID 22760701, compound

HRID 1703794Notes

Reaction equation

HRID 1703794 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(N(CC)CC)C.[N+:30]([C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)([O-:32])=[O:31]>CN(C)C=O>[N+:30]([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-:32])=[O:31]

Participants

5

Reactant 3

HCID 4831Pipemidic AcidHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 22760701HCID 22760701, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.0 g of 2-(1-piperazinyl)-8-ethyl-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid, 1.34 g of triethylamine, 2.14 g of p-nitrobenzyl bromide, and 50 ml of dimethylformamide was heated at 90° C. for 14 hours with stirring and concentrated to dryness under reduced pressure. Addition of 50 ml of water to the residue resulted in the separation of a solid, which was collected and recrystallized from dimethylformamide to give the product (2.02 g), m.p. 259°-261° C.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionAddition of 50 ml of water to the residue
  3. customresulted in the separation of a solid, which
  4. customwas collected
  5. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-d9295f6f8c5640c49d674aa17e711b54
Source dataset
uspto-grants-1978_11
Patent number
US04125615

Reaction notes

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