Hydrochloric Acid → HCID 15023844, compound

HRID 1440105Notes

Reaction equation

HRID 1440105 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:27])[C:13]2[C:18]([NH2:19])=[C:17]([F:20])[C:16]([F:21])=[C:15]([O:22][CH:23]([F:25])[F:24])[C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[H-].[Na+].Cl>O1CCCC1>[NH2:19][C:18]1[C:17]([F:20])=[C:16]([F:21])[C:15]([O:22][CH:23]([F:25])[F:24])=[C:14]2[C:13]=1[C:12](=[O:27])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 178471897ethyl 2-[2-amino-5-(difluoromethoxy)-3,4,6-trifluorobenzoyl]-3-(cyclopropylamino)prop-2-enoate

Product 1

HCID 15023844HCID 15023844, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The whole of the ethyl 3-cyclopropylamino-2-(6-amino-3-difluoromethoxy-2,4,5-trifluorobenzoyl)acrylate prepared as described above was dissolved in 340 ml of tetrahydrofuran, and 3.82 g (0.096 mole) of a 60% w/w dispersion of sodium hydride in mineral oil were added slowly to the resulting solution, whilst ice-cooling. The mixture was then stirred at the same temperature for 30 minutes, and then at room temperature for a further 1 hour. At the end of this time, the reaction mixture was acidified by the addition of 96 ml of 1N aqueous hydrochloric acid, whilst stirring vigorously. The resulting precipitate was collected by filtration and washed with water and with ethanol, in that order, to give 18.76 g of ethyl 5-amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate [(XXII), R1 =--OCHF2, R17 =C2H5, X=F] as a colorless powder, melting at 295°-296° C.

Workup

  1. temperaturecooling
  2. waitat room temperature for a further 1 hour
  3. stirringwhilst stirring vigorously
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water and with ethanol, in that order

Sources & evidence

ORD record
ord-3086631175c24ae481c7312d882371c3
Source dataset
uspto-grants-1996_03
Patent number
US05496951

Reaction notes

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