Dabco → HCID 15297666, compound

HRID 1901500Notes

Reaction equation

HRID 1901500 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.C[CH:24]1[NH:28][CH2:27][CH:26]2[CH2:29][NH:30][CH2:31][CH:25]12.[CH2:32]1N2CCN(CC2)C1>C(#N)C.CN(C)C=O>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH:17]=[CH2:18])[C:10]([F:16])=[C:11]([N:28]4[CH2:27][CH:26]5[CH:25]([CH2:31][N:30]([CH3:32])[CH2:29]5)[CH2:24]4)[C:12]=3[F:14])[C:7](=[O:19])[C:6]([C:20]([OH:22])=[O:21])=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 9237DabcoHCID 152976601-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acidHCID 22924374HCID 22924374, compound

Product 1

HCID 15297666HCID 15297666, compoundYield 80.9%

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, 0.29 g of 4-methyl-octahydropyrrolo[3,4-c]pyrrole 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. The reaction mixture is subsequently concentrated, and the residue is treated with 10 ml of water. The solid is filtered off with suction, washed with water and dried. 0.5 g of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(5-methyl-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-4-oxo-5-vinyl-3-quinolinecarboxylic acid is obtained.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated
  2. additionthe residue is treated with 10 ml of water
  3. filtrationThe solid is filtered off with suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a0898f79846d42889a6b62fdbaf51195
Source dataset
uspto-grants-1996_11
Patent number
US05578604

Reaction notes

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