Hydrochloric Acid → HCID 24753030, compound

HRID 561108Notes

Reaction equation

HRID 561108 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:33])[CH:5]=[CH:6][N:7]2[CH:30]1[CH2:32][CH2:31]1.Cl>CCO.[OH-].[Na+].O>[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:33])[CH:5]=[CH:6][N:7]2[CH:30]1[CH2:32][CH2:31]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 59002954HCID 59002954, compound

Product 1

HCID 24753030HCID 24753030, compoundYield 38.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of ethyl 2-[2-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]ethylamino]pyridine-5-carboxylate (320 mg, 0.703 mmol) in EtOH (8 mL), 1M aq. NaOH was added. The mixture was stirred at room temperature for 5 h and then stirred at 50° C. for 3 h. After cooling, the reaction mixture was diluted with water (30 mL) and neutralized with 1M HCl. The product was extracted with CH2Cl2-MeOH (5:1, 2×50 mL). The extaction mixture was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in a mixture of MeOH (50 mL) and water (50 mL), and the solution was concentrated in vacuo until ca. 30 mL. The resulting precipitate was collected by filtration, washed with water and dried to give 2-[2-[(5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinolin-7-yl)amino]ethylamino]pyridine-5-carboxylic acid (115 mg, 38%) as a yellow solid.

Workup

  1. stirringstirred at 50° C. for 3 h
  2. temperatureAfter cooling
  3. extractionThe product was extracted with CH2Cl2-MeOH (5:1, 2×50 mL)
  4. dry with materialThe extaction mixture was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in a mixture of MeOH (50 mL) and water (50 mL)
  7. concentrationthe solution was concentrated in vacuo until ca. 30 mL
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-4230caf7155347bf911f96907197db2f
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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