Dimethylformamide → HCID 86754103, compound

HRID 1415963Notes

Reaction equation

HRID 1415963 reaction equation
CN(C)C=O.[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:31])=[C:22]([N:26]4[CH2:29][CH:28]([NH2:30])[CH2:27]4)[C:23]=3[Cl:25])[C:18](=[O:32])[C:17]([C:33]([OH:35])=[O:34])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13].O.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43]([OH:46])(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(OCC)C>[C:37]1([CH3:47])[CH:38]=[CH:39][C:40]([S:43]([OH:46])(=[O:44])=[O:45])=[CH:41][CH:42]=1.[NH2:6][C:7]1[CH:8]=[C:9]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:31])=[C:22]([N:26]4[CH2:27][CH:28]([NH2:30])[CH2:29]4)[C:23]=3[Cl:25])[C:18](=[O:32])[C:17]([C:33]([OH:35])=[O:34])=[CH:16]2)[C:10]([F:14])=[CH:11][C:12]=1[F:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 9803202HCID 9803202, compound

Product 1

HCID 86754103HCID 86754103, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 0.5 ml of N,N-dimethylformamide was added 440 mg of 1-(3-amino-4,6-difluorophenyl)-7-(3-aminoazetidin-1-yl)-8-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and then 191 mg of p-toluenesulfonic acid monohydrate. The solution was stirred at room temperature. Diethyl ether was added to the reaction solution and the supernatant was removed. Ethanol was added to the residue whereupon the solid was collected by filtration and washed with diethyl ether to give 340 mg of the title compound.

Workup

  1. customthe supernatant was removed
  2. additionEthanol was added to the residue whereupon the solid
  3. filtrationwas collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-4e33b992d9e24c819e2adaeb78c23ba5
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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