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Sodium Bicarbonate → Ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1905924
Notes
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Reaction equation

HRID 1905924 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:21].[C:22]([NH:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)(=[O:24])[CH3:23].C(=O)(O)[O-].[Na+]>C(#N)C>[C:22]([NH:25][CH:26]1[CH2:30][CH2:29][N:28]([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]3[CH:12]3[CH2:14][CH2:13]3)=[CH:4][C:3]=2[F:21])[CH2:27]1)(=[O:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5227153-AcetamidopyrrolidineHCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 13456047Ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (1.24 g), 3-acetylaminopyrrolidine (563 mg), sodium bicarbonate (437 mg) and acetonitrile (40 ml) was refluxed for 30 minutes. After evaporation to dryness under reduced pressure, water was added to the residue. The resulting crystals were filtered and recrystallized from ethanolisopropyl ether to give ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (1.50 g), m.p. 246°-248° C.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customAfter evaporation to dryness under reduced pressure, water
  3. additionwas added to the residue
  4. filtrationThe resulting crystals were filtered
  5. customrecrystallized from ethanolisopropyl ether

Sources & evidence

ORD record
ord-3a84edf6fccf43d1bf17371d83cc03aa
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04649144

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes