Dimethylformamide → HCID 67915570, compound

HRID 465388Notes

Reaction equation

HRID 465388 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[C:22]([O:26][C:27]([N:29]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH3:35]N(C=O)C.[H-].[Na+]>C(Cl)(Cl)Cl>[C:22]([O:26][C:27]([N:29]1[CH:33]=[CH:32][CH:35]=[C:31]([O:34][C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[C:9]([NH2:17])[C:10]=2[F:16])[CH2:30]1)=[O:28])([CH3:23])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 44169391-Boc-3-pyrrolidinolHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 67915570HCID 67915570, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1.20 g of 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.50 g of 1-t-butoxycarbonyl-3-hydroxypyrrolidine and 1,5 ml of DMF was added 483 mg of 55% sodium hydride while the former was stirred under ice cooling. The resultant mixture was stirred for further 20 hours at room temperature. The reaction mixture was diluted with chloroform and then successively washed with 10% aq. citric acid solution and saturated saline. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue thus obtained was recrystallized from ethanol, whereby 1.48 g of the title compound was obtained as pale green powder.

Workup

  1. washsuccessively washed with 10% aq. citric acid solution and saturated saline
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8778d8641cef4d93bf7a5aa5c4eb3bfe
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

Loading…