Triethylamine → 5-Amino-7-(3-methylaminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid

HRID 729068Notes

Reaction equation

HRID 729068 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.Cl.[CH3:24][NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1.C(N(CC)CC)C>C(#N)C.CN(C)C=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:28]2[CH2:29][CH2:30][CH2:31][CH:26]([NH:25][CH3:24])[CH2:27]2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 67928794N-Methylpiperidin-3-amine hydrochloride

Product 1

HCID 156706925-Amino-7-(3-methylaminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acidYield 29.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (1.039 g), 3-methylaminopiperidine hydrochloride (1.5 g) and triethylamine (2.5 g) in acetonitrile (30 ml) and N,N-dimethylformamide (10 ml) was refluxed overnight. Concentration of thereaction mixture followed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1) gave a yellow crystalline substance [MS m/e: 404 (M+)]. The crystalline substance thus obtained was recrystallized from ethanol to afford 5-amino-7-(3-methylaminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (400 mg) as yellow needles. m.p. 265°-275° C. (decomposition).

Workup

  1. temperaturewas refluxed overnight
  2. customConcentration of thereaction mixture followed by purification by silica gel column chromatography (chloroform:methanol:ammonium hydroxide=15:5:1)
  3. customgave a yellow crystalline substance [MS m/e: 404 (M+)]
  4. customThe crystalline substance thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-c1b6fa847bc34087ba4e6bd6bde48bdc
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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