Acetic Acid → HCID 53724661, compound

HRID 344853

Reaction equation

HRID 344853 reaction equation
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][NH:33][CH2:32][CH2:31][NH:30]2)=[CH:25][CH:24]=1.O.C(O)(=O)C>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:33]2[CH2:32][CH2:31][NH:30][CH:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH2:34]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 46176232-(4-Fluorophenyl)piperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 53724661HCID 53724661, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

A suspension of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.6 g) and (RS)-2-(4-fluorophenyl)piperazine (3.7 g) in pyridine (16 cc) is heated to a temperature in the region of 115° C. for 24 hours. The reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 60° C. The residue is taken up with ethanol (40 cc) and concentrated again under reduced pressure under the above conditions. The solid obtained is taken up with water (10 cc), treated with 10% strength acetic acid (1.75 cc), drained and washed with water (2×10 cc) and ethanol (2×10 cc). After 2 recrystallizations in dimethylformamide (10 cc each time), (RS)-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b ][1,8]naphthyridine-3-carboxylic acid (1.1 g) is obtained in the form of a yellow solid, m.p. 270°-275° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 60° C
  2. concentrationconcentrated again under reduced pressure under the above conditions
  3. customThe solid obtained
  4. washwashed with water (2×10 cc) and ethanol (2×10 cc)
  5. customAfter 2 recrystallizations in dimethylformamide (10 cc each time)

Sources & evidence

ORD record
ord-86f51b4aa94f4fa0959685c631bcb861
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Linked notes

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