Triethylamine → 7-[4-(2-Hydroxyethylidene)piperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 15504Notes

Reaction equation

HRID 15504 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.Cl[C:9]1[N:18]=[C:17]2[C:12]([C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15][N:16]2[CH:19]2[CH2:21][CH2:20]2)=[CH:11][C:10]=1[F:26]>C(#N)C>[OH:23][CH2:22][CH:14]=[C:13]1[CH2:5][CH2:4][N:3]([C:9]2[N:18]=[C:17]3[C:12]([C:13](=[O:25])[C:14]([C:22]([OH:24])=[O:23])=[CH:15][N:16]3[CH:19]3[CH2:21][CH2:20]3)=[CH:11][C:10]=2[F:26])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 593424447-[4-(2-Hydroxyethylidene)piperidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of amine 103 (256 mg, 1.06 mmol) and triethylamine (0.5 mL, 3.55 mmol) in acetonitrile (4 mL) was treated with 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-naphthyridine-3-carboxylic acid (200 mg, 0.71 mmol) under nitrogen and the reaction mixture was allowed to stir for 16 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3×10 mL) and allowed to dry overnight to afford the title compound 163 (105 mg, 40%). MS 374 (M+H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. washthe residue was washed with water (3×10 mL)
  3. customto dry overnight

Sources & evidence

ORD record
ord-d6cbd9c94be14219b07239531cfb199d
Source dataset
uspto-grants-2010_06
Patent number
US07732612B2

Reaction notes

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