Water → HCID 22114870, compound

HRID 1276057Notes

Reaction equation

HRID 1276057 reaction equation
O.C(OCC)(=O)C.[Br:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]3[CH:29]=[CH:30][N:31]=[C:19]23)=[C:11]([F:32])[CH:10]=1>[Fe].C(O)(=O)C>[NH2:15][C:14]1[C:9]([Br:8])=[CH:10][C:11]([F:32])=[C:12]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]3[CH:29]=[CH:30][N:31]=[C:19]23)[CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 22114877HCID 22114877, compound

Product 1

HCID 22114870HCID 22114870, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixed solution of water (100 ml), ethyl acetate (50 ml) and acetic acid (50 ml) was added 8-(4-bromo-2-fluoro-5-nitrophenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (12.5 g) synthesized in Example 16 and iron powder (8.0 g) and heated to reflux for 3 hours. The reaction solution was filtered through Celite and then the Celite was washed with heated ethyl acetate. The combined filtrate and washing was washed with water, saturated sodium hydrogencarbonate and water in this order, and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure after removing a portion adjacent to the original point of the short column of alumina. The thus obtained solid was recrystallized from isopropyl alcohol/isopropyl ether=1/9 to give the compound of interest (9.3 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. filtrationThe reaction solution was filtered through Celite
  4. washthe Celite was washed with heated ethyl acetate
  5. washThe combined filtrate and washing
  6. washwas washed with water, saturated sodium hydrogencarbonate and water in this order
  7. dry with materialdried on anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customafter removing a portion adjacent to the original point of the short column of alumina
  10. customThe thus obtained solid was recrystallized from isopropyl alcohol/isopropyl ether=1/9
  11. customto give the compound of interest (9.3 g)

Sources & evidence

ORD record
ord-e933e71172434429874030b9d5bec9fd
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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