Dabco → HCID 15297666, compound

HRID 2258129Notes

Reaction equation

HRID 2258129 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-c83ff86604da43b3b67fbc360627d55b
Source dataset
uspto-grants-1997_08
Patent number
US05659038

Reaction notes

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