Acetonitrile → 7-(1-tert-Butoxycarbonylamino-3-azabicyclo[4.1.0]-hept-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester

HRID 275207Notes

Reaction equation

HRID 275207 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH:14]1[CH2:13][CH2:12][NH:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[N:26]=[C:25]2[C:20]([C:21](=[O:38])[C:22]([C:35]([OH:37])=[O:36])=[CH:23][N:24]2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])=[CH:19][C:18]=1[F:39].[C:40](#N)[CH3:41]>>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH:14]1[CH2:13][CH2:12][N:11]([C:17]1[N:26]=[C:25]3[C:20]([C:21](=[O:38])[C:22]([C:35]([O:37][CH2:40][CH3:41])=[O:36])=[CH:23][N:24]3[C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])=[CH:19][C:18]=1[F:39])[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 20089946tert-Butyl 3-azabicyclo[4.1.0]heptan-1-ylcarbamate

Product 1

HCID 867463427-(1-tert-Butoxycarbonylamino-3-azabicyclo[4.1.0]-hept-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl esterYield 88%

Procedure

A solution of 1-tert-butoxycarbonylamino-3-azabicyclo[4.1.0]heptane (200 mg, 0.94 mmol) and the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (327 mg, 0.85 mmol) in acetonitrile (12 ml) was heated at reflux for 3 hours. Solvent was removed in vacuo, and the residue was chromatographed on silica gel (eluant: 50% ethyl acetate/hexane) to afford the title product as an off-white solid (423 mg, 0.758 mmol, 88% yield).

Workup

  1. temperatureat reflux for 3 hours
  2. customSolvent was removed in vacuo
  3. customthe residue was chromatographed on silica gel (eluant: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4fd1f2f294dc420d8aa7b34e18146126
Source dataset
uspto-grants-1995_02
Patent number
US05391763

Reaction notes

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