Water → 7-(4-Methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid

HRID 1901499Notes

Reaction equation

HRID 1901499 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH:17]=[CH2:18])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:19])[C:6]([C:20]([OH:22])=[O:21])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:23][NH:24][CH:25]1[CH:33]=[CH:32][CH2:31][CH:30]2[CH:26]1[CH2:27][NH:28][CH2:29]2.C1N2CCN(CC2)C1.O>C(#N)C.CN(C)C=O>[CH3:23][NH:24][CH:25]1[CH:33]=[CH:32][CH2:31][CH:30]2[CH:26]1[CH2:27][N:28]([C:11]1[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:19])[C:6]([C:20]([OH:22])=[O:21])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([CH:17]=[CH2:18])[C:10]=1[F:16])[CH2:29]2

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 15283247HCID 15283247, compoundHCID 152976601-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid

Product 1

HCID 152976657-(4-Methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acidYield 76.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

0.46 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid, 0.34 g of 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole and 0.18 g of DABCO are refluxed for 2 hours in a mixture of 3 ml of acetonitrile and 1.5 ml of dimethylformamide. At room temperature, the reaction mixture is treated with 20 ml of water, and the product is filtered off with suction, washed with water and dried. 0.5 g of 7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid is obtained.

Workup

  1. filtrationthe product is filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-fe534adcd864464296d233e46e8bfab9
Source dataset
uspto-grants-1996_11
Patent number
US05578604

Reaction notes

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