Sodium hydride → HCID 22129990, compound

HRID 1857645Notes

Reaction equation

HRID 1857645 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[C:9]([C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=3)[C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[N+:30]([O-:32])=[O:31].Cl.Cl[CH2:35][CH2:36][CH:37]1[CH2:41][CH2:40][CH2:39][N:38]1[CH3:42]>CN(C)C=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([N:23]([CH2:35][CH2:36][CH:37]3[CH2:41][CH2:40][CH2:39][N:38]3[CH3:42])[C:24](=[O:29])[C:25]([F:28])([F:26])[F:27])=[C:9]([C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=3)[C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[N+:30]([O-:32])=[O:31]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 22129987HCID 22129987, compound

Product 1

HCID 22129990HCID 22129990, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 10 mg sodium hydride in 1.0 mL N,N-dimethylformamide was added 90 mg N-[7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl]-2,2,2-trifluoroacetamide and the mixture stirred at room temperature for 1 hour. At this time, 75 mg of 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride and the mixture heated to 80° C. on an oil bath. After 6 hours, the mixture was cooled to room temperature, diluted with ethyl acetate and extracted with water. The organic portion was washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 95:5+1% ammonium hydroxide) gave the title compound (50 mg).

Workup

  1. waitAfter 6 hours
  2. temperaturethe mixture was cooled to room temperature
  3. extractionextracted with water
  4. washThe organic portion was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 95:5+1% ammonium hydroxide)

Sources & evidence

ORD record
ord-d78c2351ed394b76abaef00e88fa9606
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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