HCID 20071502, compound → HCID 15136279, compound

HRID 981292Notes

Reaction equation

HRID 981292 reaction equation
C([NH:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:14]3[CH:15]([CH3:18])[CH2:16][O:17][C:12]([C:13]=23)=[C:11]([CH:27]2[CH2:29][CH2:28]2)[C:10]=1[F:30])C1C=CC=CC=1.[H][H]>C(O)(=O)C.[C].[Pd]>[NH2:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]([C:24]([OH:26])=[O:25])=[CH:19][N:14]3[CH:15]([CH3:18])[CH2:16][O:17][C:12]([C:13]=23)=[C:11]([CH:27]2[CH2:28][CH2:29]2)[C:10]=1[F:30]

Participants

5

Reactant 2

HCID 20071502HCID 20071502, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15136279HCID 15136279, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In 5 ml of acetic acid was dissolved 50 mg of 8-benzylamino-10-cyclopropyl-9-fluoro-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 50 mg of 5% palladium-carbon. The resulting mixture was stirred at room temperature for 1.5 hours at atmospheric pressure in a hydrogen stream. The reaction mixture was filtered. The filtrate was concentrated to dryness under reduced pressure. Ethanol was added to the residue obtained. The resulting crystals were collected by filtration to obtain 19.7 mg (yield: 50.5%) of 8-amino-10-cyclopropyl9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid. Melting point: >280° C. (recrystallized from chloroform-ethanol)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated to dryness under reduced pressure
  3. additionEthanol was added to the residue
  4. customobtained
  5. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-4807104fa3624f6ea23f0e2b8f5ec4f7
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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