Water → 7-(4-Amino-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 1901498Notes

Reaction equation

HRID 1901498 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.[NH2:23][CH:24]1[CH:32]=[CH:31][CH2:30][CH:29]2[CH:25]1[CH2:26][NH:27][CH2:28]2.C1N2CCN(CC2)C1.O>C(#N)C.CN(C)C=O>[NH2:23][CH:24]1[CH:32]=[CH:31][CH2:30][CH:29]2[CH:25]1[CH2:26][N:27]([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])[CH2:28]2

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 152832494-Amino-1,3,3a,4,7,7a-hexahydro-isoindoleHCID 152976601-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid

Product 1

HCID 229243837-(4-Amino-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 77.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

0.93 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acid, 0.62 g of 4-amino-1,3,3a,4,7,7a-hexahydro-isoindole and 0.34 g of DABCO are refluxed for 1 hour in a mixture of 6 ml of acetonitrile and 3 ml of dimethylformamide. The reaction mixture is treated with 20 ml of water, and the product is filtered off with suction, washed with water and dried. 1 g of 7-(4-amino-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-26f0414297f94f4a81e36dab77db6da7
Source dataset
uspto-grants-1996_11
Patent number
US05578604

Reaction notes

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