Acetonitrile → HCID 53978682, compound

HRID 369300Notes

Reaction equation

HRID 369300 reaction equation
[CH2:1]([N:3]([CH2:6]C)CC)[CH3:2].[NH2:8][C:9]1[C:10]([F:33])=[CH:11][C:12]([F:32])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22](F)[C:23]=3[Cl:25])[C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16]2)[CH:14]=1.C(#[N:36])C>>[NH2:36][CH2:2][CH2:1][N:3]([C:22]1[C:23]([Cl:25])=[C:24]2[C:19]([C:18](=[O:28])[C:17]([C:29]([OH:31])=[O:30])=[CH:16][N:15]2[C:13]2[CH:14]=[C:9]([NH2:8])[C:10]([F:33])=[CH:11][C:12]=2[F:32])=[CH:20][C:21]=1[F:27])[CH3:6]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 53978682HCID 53978682, compound

Conditions

Temperature
60 °C

Procedure

N-Methylenediamine (17 mg) and triethylamine (35 mg) were added to acetonitrile (5 ml), to which 1-(5-amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg) was added with heating and stirring at 60° C. The resultant mixture was heated under reflux for 2 hours as it was. After the reaction mixture was allowed to cool, solids deposited were collected by filtration and washed with ethanol and diethyl ether to obtain the title compound (40 mg) as a pale brown powder.

Workup

  1. additionwas added
  2. temperaturewith heating
  3. temperatureunder reflux for 2 hours as it
  4. temperatureto cool
  5. filtrationsolids deposited were collected by filtration
  6. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-99fb077d6a2644639f8d3fdf5029ffdc
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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