Hydrochloric Acid → HCID 9985204, compound

HRID 981290Notes

Reaction equation

HRID 981290 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:16]([F:34])=[C:17](F)[C:18]3[C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:20]4[CH:21]([CH3:25])[CH2:22][O:23][C:24]=2[C:19]=34)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(OCC)(=O)C.Cl>CN(C)C=O.O>[CH2:35]([NH:42][C:17]1[C:18]2[C:28](=[O:29])[C:27]([C:30]([OH:32])=[O:31])=[CH:26][N:20]3[CH:21]([CH3:25])[CH2:22][O:23][C:24]([C:19]=23)=[C:15]([C:12]2([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:14][CH2:13]2)[C:16]=1[F:34])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 10050381HCID 10050381, compound

Product 1

HCID 9985204HCID 9985204, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 2 ml of N,N-dimethylformamide was dissolved 200 mg of 10-(1-benzyloxycarbonylaminocyclopropyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid. To the resulting solution was added 319 mg of benzylamine. The resulting mixture was stirred at 90°-100° C. for 4.5 hours. The reaction mixture was added to a mixture of 5 ml of ethyl acetate and 5 ml of water. The resulting mixture was adjusted to pH 1 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 and the resulting crystals were collected by filtration to obtain 110 mg (yield: 46.4%) of 8-benzylamino-10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro- 3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid.

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-e20cdb951de24352ab0338b5bc84bb2f
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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