Water → 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(octahydro-pyrrolo[3,4-b]pyrrolizin-2-yl)-4-oxo-5-vinyl-3-quinolinecarboxylic acid

HRID 1901501Notes

Reaction equation

HRID 1901501 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.[CH2:23]1[CH:27]2[CH2:28][CH:29]3[N:33]([CH:26]2[CH2:25][NH:24]1)[CH2:32][CH2:31][CH2:30]3.C1N2CCN(CC2)C1.O>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:24]4[CH2:25][CH:26]5[CH:27]([CH2:28][CH:29]6[N:33]5[CH2:32][CH2:31][CH2:30]6)[CH2:23]4)[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

Participants

7

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 152976601-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-5-vinyl-3-quinolinecarboxylic acidHCID 16227934Decahydropyrrolo[3,4-b]pyrrolizine

Product 1

HCID 229243681-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(octahydro-pyrrolo[3,4-b]pyrrolizin-2-yl)-4-oxo-5-vinyl-3-quinolinecarboxylic acidYield 52.7%

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, 0.69 g of decahydropyrrolo[3,4-b]pyrrolizine and 0.36 g of DABCO are refluxed for 2 hours in a mixture of 6 ml of acetonitrile and 3 ml of dimethylformamide. At room temperature, the reaction mixture is treated with 20 ml of water, and the solid is filtered off with suction, washed with water and dried. 0.7 g of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(octahydro-pyrrolo[3,4-b]pyrrolizin-2-y1)-4-oxo-5-vinyl-3-quinolinecarboxylic acid is obtained.

Workup

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

Sources & evidence

ORD record
ord-7406ecb01aeb43eda53a6d64e423feda
Source dataset
uspto-grants-1996_11
Patent number
US05578604

Reaction notes

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