N4-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-aminoisonicotinamide → N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-8-carboxamide

HRID 1828442Notes

Reaction equation

HRID 1828442 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:20](OC1C=CC(Cl)=C(Cl)C=1Cl)(=[O:25])[CH2:21][C:22]([O-])=[O:23]>C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:12]2[CH:17]=[CH:16][N:15]3[C:20](=[O:25])[CH2:21][C:22](=[O:23])[N:18]=[C:14]3[CH:13]=2)=[O:19])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 22063525N4-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-aminoisonicotinamideHCID 22063717Trichlorophenyl malonate

Product 1

HCID 22063754N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-8-carboxamideYield 84%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

N4-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-aminoisonicotinamide (200 mg, 0.724 mmol) was added with xylene (20 ml) and trichlorophenyl malonate (370 mg, 0.796 mmol) and refluxed by heating at 130° C. The reaction solution was stirred for 1 hour, then returned to room temperature and concentrated under reduced pressure. The resulting orange crystals was taken by filtration, washed with chloroform, dried under reduced pressure to obtain 209 mg (84%) of the title compound as orange crystals without purification.

Workup

  1. temperaturerefluxed
  2. customreturned to room temperature
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe resulting orange crystals was taken by filtration
  5. washwashed with chloroform
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fcd8f059b5fe4effa3a35423e0f94982
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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