N-methyl-2-pyrrolidone → HCID 10108715, compound

HRID 1837346Notes

Reaction equation

HRID 1837346 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1OCCOC)[N:15]=[CH:14][C:13]([C:24]#[N:25])=[C:12]2Cl)C1C=CC=CC=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CN1CCCC1=[O:40]>>[CH3:1][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[N:31]1[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]1)[NH:15][CH:14]=[C:13]([C:24]#[N:25])[C:12]2=[O:40]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 531671-MethylpiperazineHCID 23498112HCID 23498112, compound

Product 1

HCID 10108715HCID 10108715, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 200 mg (0.92 mmol) of 7-fluoro-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile (Reference Example 24) and 551 mg (5.50 mmol) of N-methylpiperazine in 1 mL of 1-methyl-2-pyrrolidinone is heated at 90° C. for 8 hours, then at 105° C. for a further 16 hours. The solvents are removed in vacuo. To the resulting oily residue was added 2 mL of water and 5 mL of methanol. The solvents are again removed in vacuo. The crude product is purified by silica gel chromatography utilizing a gradient of methylene chloride/methanol (9:1 to 4:1) to yield 152 mg of 6-methoxy-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carbonitrile as a yellow solid, dec.>235° C.

Workup

  1. customThe solvents are removed in vacuo
  2. additionTo the resulting oily residue was added 2 mL of water and 5 mL of methanol
  3. customThe solvents are again removed in vacuo
  4. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-f210c17c8083421a827c15f6c8f32796
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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