HCID 69103219, compound → 851087-60-0

HRID 2217237Notes

Reaction equation

HRID 2217237 reaction equation
[NH2:1][C:2]1[C:3](C(O)=O)=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1>ClC1C=CC=CC=1Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([CH:22]([CH3:24])[CH3:23])[CH:16]=2)=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 69103219HCID 69103219, compound

Product 1

HCID 24810000851087-60-0Yield 88.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
167.5 °C

Procedure

3-Amino-5-(4-fluorophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-2-pyrazinecarboxylic acid (25 g) was suspended in 1,2-dichlorobenzene (125 ml). The suspension was heated at 165-170° C. with stirring for 4 hours. The reaction mixture was cooled to 20-25° C. To the cooled mixture was added IPE (250 ml). The suspension was stirred at 25-30° C. for 3 hours. The precipitate was collected by filtration and dried in vacuo. The above dried precipitate was purified by chromatography on silica gel (500 g) eluting with CHCl3:MeOH (9:1, 21). Evaporation of solvent in vacuo gave yellowish crystal residue, which was recrystallized from 70% EtOH (322 ml) to give 5-[5-amino-3-(4-fluorophenyl)-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone as yellowish crystal (19.4 g).

Workup

  1. temperatureThe reaction mixture was cooled to 20-25° C
  2. additionTo the cooled mixture was added IPE (250 ml)
  3. stirringThe suspension was stirred at 25-30° C. for 3 hours
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo
  6. customThe above dried precipitate
  7. customwas purified by chromatography on silica gel (500 g)
  8. washeluting with CHCl3:MeOH (9:1, 21)
  9. customEvaporation of solvent in vacuo
  10. customgave yellowish crystal residue, which
  11. customwas recrystallized from 70% EtOH (322 ml)

Sources & evidence

ORD record
ord-43eca26d54c640078c842406d6a94cd1
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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