Sodium Chloride → HCID 24753032, compound

HRID 561109Notes

Reaction equation

HRID 561109 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][N:18]=2)[C:9]([O:28][CH3:29])=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([C:33]([OH:35])=[O:34])=[CH:6][N:7]2[CH:30]1[CH2:32][CH2:31]1.[Na+].[Cl-]>CO.[OH-].[Na+].O.[NH4+].[Cl-]>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=2)[C:9]([O:28][CH3:29])=[C:8]2[C:3]=1[C:4](=[O:36])[C:5]([C:33]([OH:35])=[O:34])=[CH:6][N:7]2[CH:30]1[CH2:31][CH2:32]1

Participants

7

Reactant 2

HCID 5234Sodium ChlorideHCID 59003047HCID 59003047, compound

Product 1

HCID 24753032HCID 24753032, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a suspension of 5-amino-1-cyclopropyl-7-[2-[(5-ethoxycarbonyl-2-pyridyl)amino]ethylamino]-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (390 mg, 0.781 mmol) in MeOH (5 mL), 1M aq. NaOH (5 mL) was added. The mixture was stirred at room temperature for 8 h. The reaction mixture was diluted with water (30 mL) and saturated aq NH4Cl (20 mL). The solution was saturated with NaCl and the crude product was extracted with EtOAc (2×100 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and evaporated. The residue was dissolved in a mixture of MeOH (100 mL) and water (30 mL). The solution was concentrated in vacuo until ca. 50 mL and the resulting precipitate was collected by filtration, washed with water and dried to give 5-amino-1-cyclopropyl-6-fluoro 1,4-dihydro-7-[2-[(5-hydroxycarbonyl-2-pyridyl)amino]ethylamino]-8-methoxy-4-oxoquinoline-3-carboxylic acid (86.6 mg, 24%) as a yellow solid.

Workup

  1. additionwas added
  2. extractionthe crude product was extracted with EtOAc (2×100 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. dissolutionThe residue was dissolved in a mixture of MeOH (100 mL) and water (30 mL)
  7. concentrationThe solution was concentrated in vacuo until ca. 50 mL
  8. filtrationthe resulting precipitate was collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-7470c996bf2b45feb8d2807a53d3801d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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