Sodium Methoxide → 7-[3-(Acetylamino)-1-piperidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

HRID 729065Notes

Reaction equation

HRID 729065 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[C:20](F)=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:24][CH2:23]3)=[CH:13][C:12]=2[F:29])[CH2:6]1)(=[O:3])[CH3:2].[CH3:30][O-:31].[Na+]>CN(C)C=O>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[C:20]([O:31][CH3:30])=[C:19]3[C:14]([C:15](=[O:28])[C:16]([C:25]([OH:27])=[O:26])=[CH:17][N:18]3[CH:22]3[CH2:23][CH2:24]3)=[CH:13][C:12]=2[F:29])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15670689HCID 15670689, compound

Product 1

HCID 156706907-[3-(Acetylamino)-1-piperidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(3-acetamidopiperidin-1-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (4.05 g), sodium methoxide (2.16 g) and N,N-dimethylformamide (120 ml) was stirred for 2 hours at 100°-140° C. The reaction mixture was concentrated in vacuumand water was added to the residue. The mixture was neutralized with 1N hydrochloric acid and the neutralized mixture was then concentrated in vacuum. Purification of the concentrated mixture by silica gel column chromatography (chloroform-methanol) gave 7-(3-acetamidopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid. m.p. 248°-250° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuumand water
  2. additionwas added to the residue
  3. concentrationthe neutralized mixture was then concentrated in vacuum
  4. customPurification of the concentrated mixture by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-75f80f9023b04b808b9b48e9a97f7d3e
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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