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N-Methylpiperidine → HCID 10167035, compound

HRID 2417237
Notes
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Reaction equation

HRID 2417237 reaction equation
[C:1]([NH:4][C:5]1[C:14]([F:15])=[C:13](F)[C:12]([CH3:17])=[C:11]2[C:6]=1[C:7](=[O:25])[C:8]([C:22]([OH:24])=[O:23])=[CH:9][N:10]2[C@@H:18]1[CH2:20][C@@H:19]1[F:21])(=[O:3])[CH3:2].[C:26]([O:30][C:31]([NH:33][C:34]1([C@H:37]2[CH2:41][NH:40][CH2:39][C@H:38]2[F:42])[CH2:36][CH2:35]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CN1CCCCC1>CS(C)=O>[C:1]([NH:4][C:5]1[C:14]([F:15])=[C:13]([N:40]2[CH2:41][C@H:37]([C:34]3([NH:33][C:31]([O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:32])[CH2:35][CH2:36]3)[C@H:38]([F:42])[CH2:39]2)[C:12]([CH3:17])=[C:11]2[C:6]=1[C:7](=[O:25])[C:8]([C:22]([OH:24])=[O:23])=[CH:9][N:10]2[C@@H:18]1[CH2:20][C@@H:19]1[F:21])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12291N-MethylpiperidineHCID 10247537HCID 10247537, compoundHCID 11075684HCID 11075684, compound

Product 1

HCID 10167035HCID 10167035, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A dimethyl sulfoxide (15 ml) solution containing 5-acetylamino-6,7-difluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (3.0 g, 8.47 mmol), (3S,4R)-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-fluoropyrrolidine (3.19 g, 12.7 mmol) and 1-methylpiperidine (1.54 ml, 12.7 mmol) was heated at an outer temperature of 80° C. for 22 hours under a condition of 2.94×108 Pa. The reaction solution was washed with ethyl acetate to adjust the total volume to 128 ml and then washed twice with 5% citric acid aqueous solution (30 ml) to separate the organic phase and aqueous phase. The aqueous phase was extracted three times with ethyl acetate, combined with the above organic phase and then extracted three times with 5% potassium hydroxide aqueous solution (30 ml). To the aqueous phase were added chloroform (90 ml) and then 3 N hydrochloric acid until pH became 4, thereby separating the organic phase and aqueous phase. The aqueous phase was extracted twice with chloroform, combined with the above organic phase and then dried over anhydrous sodium sulfate. By evaporating the solvent under a reduced pressure, 5-acetylamino-7-[(3S,4R)-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-fluoropyrrolidinyl]-6-fluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid (4.92 g, purity 90.0%, yield 89.2%) was obtained as yellow amorphous.

Workup

  1. washThe reaction solution was washed with ethyl acetate
  2. washwashed twice with 5% citric acid aqueous solution (30 ml)
  3. customto separate the organic phase and aqueous phase
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. extractionextracted three times with 5% potassium hydroxide aqueous solution (30 ml)
  6. additionTo the aqueous phase were added chloroform (90 ml)
  7. customseparating the organic phase and aqueous phase
  8. extractionThe aqueous phase was extracted twice with chloroform
  9. dry with materialdried over anhydrous sodium sulfate
  10. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-0eddab7abbe14f0d93afe5ad399f657e
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825353B2

Reaction notes

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