Hydrochloric Acid → HCID 15136295, compound

HRID 981280Notes

Reaction equation

HRID 981280 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:24](F)=[C:23]3[C:18]([C:19](=[O:36])[C:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:21][N:22]3[C@@H:26]([CH3:30])[CH2:27][NH:28][CH3:29])=[CH:17][C:16]=2[F:37])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.Cl>CN(C)C=O.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:24]3[N:28]([CH3:29])[CH2:27][C@H:26]([CH3:30])[N:22]4[CH:21]=[C:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:19](=[O:36])[C:18]([C:23]=34)=[CH:17][C:16]=2[F:37])[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 54166271HCID 54166271, compound

Product 1

HCID 15136295HCID 15136295, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 5 ml of N,N-dimethylformamide was dissolved 240 mg of ethyl (S)-7-(1-benzyloxycarbonylaminocyclopropyl)-6,8-difluoro-1-[2-(N-methylamino)-1-methylethyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate. To the resulting solution was added 80 mg of potassium carbonate. The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was added to a mixture of 20 ml of ethyl acetate and 20 ml of water. The resulting mixture was adjusted to pH 3 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. Diethyl ether was added to the residue obtained. The resulting crystals were collected by filtration to obtain 120 mg (yield: 52.2%) of ethyl (S)-10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-1,3-dimethyl-7-oxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxylate.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. customobtained
  7. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-90d0b3b15fc64853af11a7cf763b41b3
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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