Hydrochloric Acid → HCID 15870851, compound

HRID 1584835Notes

Reaction equation

HRID 1584835 reaction equation
C(OC([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[C:29]([CH2:30][F:31])=[C:28]4[C:23]([C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26][N:27]4[CH:32]4[CH2:34][CH2:33]4)=[CH:22][C:21]=3[F:39])[CH:17]=2)[CH2:12]1)=O)C1C=CC=CC=1.Cl>Br.C(O)(=O)C.[OH-].[Na+]>[CH:32]1([N:27]2[C:28]3[C:23](=[CH:22][C:21]([F:39])=[C:20]([C:16]4[CH:17]=[C:18]5[C:13](=[CH:14][CH:15]=4)[CH2:12][NH:11][CH2:19]5)[C:29]=3[CH2:30][F:31])[C:24](=[O:38])[C:25]([C:35]([OH:37])=[O:36])=[CH:26]2)[CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21220299HCID 21220299, compound

Product 1

HCID 15870851HCID 15870851, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

In 3.2 ml of 30% hydrogen bromide-acetic acid solution was suspended 0.16 g of 7-[2-(benzyloxycarbonyl)isoindolin-5-yl]-1-cyclopropyl-6-fluoro-8-fluoromethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, and the suspension was stirred at room temperature for 40 minutes. The reaction mixture was concentrated under reduced pressure and to the residue was added ethanol, and the crystals formed were collected by filtration. The crystals obtained were dissolved in dilute aqueous sodium hydroxide solution, and the pH was adjusted to 7 with dilute hydrochloric acid. The crystals precipitated were collected by filtration, to obtain 68 mg of colorless, crystalline 1-cyclopropyl-6-fluoro-8-fluoromethyl-7-(isoindolin-5-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and to the residue
  2. additionwas added ethanol
  3. customthe crystals formed
  4. filtrationwere collected by filtration
  5. customThe crystals obtained
  6. customThe crystals precipitated
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5342041715f04e61b428cb286a67d9a8
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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