Hydrochloric Acid → HCID 13821774, compound

HRID 246937Notes

Reaction equation

HRID 246937 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:19]([F:20])=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[C:12]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[F:29])[N:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+].O.Cl>CO>[F:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[NH:21][C:12]1[N:11]=[C:10]([N:7]2[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]2)[C:19]([F:20])=[CH:18][C:13]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 13821763HCID 13821763, compound

Product 1

HCID 13821774HCID 13821774, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 3.9 ml of methanol was suspended 130 mg of methyl 6-(4-acetyl-1-piperazinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate, and 3.33 ml of 2N aqueous sodium hydroxide solution was added thereto, after which the resulting mixture was subjected to reaction under reflux for 2 hours. To the reaction mixture was added 2 ml of water, and the pH thereof was adjusted to 8.5 with 1N hydrochloric acid, after which the crystals thus deposited were collected by filtration and washed with 2 ml of water to obtain 110 mg (yield 98.2%) of 2-(2,4-difluorophenylamino)-5-fluoro-6-(1-piperazinyl)nicotinic acid having a melting point of 279°-281° C.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2 hours
  4. filtrationafter which the crystals thus deposited were collected by filtration
  5. washwashed with 2 ml of water

Sources & evidence

ORD record
ord-1e831ec217744189aa4d6d8f56827fda
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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