Potassium Carbonate → i-Propyl 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-amino-3',3'-dimethyl-piperidin-1-yl)-4-oxo-quinoline-3-carboxylate

HRID 11303Notes

Reaction equation

HRID 11303 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH:22]C(OC(C)(C)C)=O)[C:18]([CH3:31])([CH3:30])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:33])[C:6]([C:34]([OH:36])=[O:35])=[CH:5]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].I[CH2:44][CH2:45][CH3:46]>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:32])=[C:11]([N:16]4[CH2:21][CH2:20][CH:19]([NH2:22])[C:18]([CH3:30])([CH3:31])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:33])[C:6]([C:34]([O:36][CH:45]([CH3:46])[CH3:44])=[O:35])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 103007861-Cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-t-butoxycarbonylamino-3',3'-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

Product 1

HCID 86760219i-Propyl 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4'-amino-3',3'-dimethyl-piperidin-1-yl)-4-oxo-quinoline-3-carboxylateYield 45%

Conditions

Temperature
70 °C

Procedure

In a dry dimethylformaide (15 ml) was taken a mixture of 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-t-butoxycarbonylamino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid (1 g, 1.98 mmole), K2CO3 (0.275 g, 1.98 mmole) was stirred at 70° C. for 7 hr. Added 1-iodopropane (0.5 g, 2.98 mmole) to reaction mixture and stirred at the same temperature for 16 hr. Solvent was concentrated up to dryness and (15 ml) water was added to it and extracted with chloroform (25 ml×2). Organic layer was separated, dried, concentrated, Which was hydrolysied with trifluoroacetic acid in methylene dichloride and purified on silica column to furnish titled product. Yield 45%, m.p 140–42° C., C24H32FN3O4, m/z 446 (M+1).

Workup

  1. stirringstirred at the same temperature for 16 hr
  2. concentrationSolvent was concentrated up to dryness and (15 ml) water
  3. additionwas added to it
  4. extractionextracted with chloroform (25 ml×2)
  5. customOrganic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. custompurified on silica column

Sources & evidence

ORD record
ord-a1b74487e4a6436087218ffd783f010b
Source dataset
uspto-grants-2006_08
Patent number
US07098219B2

Reaction notes

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