Hydrochloric Acid → 4-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid

HRID 1783453Notes

Reaction equation

HRID 1783453 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+].O.Cl>C(O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:24])=[O:3])=[CH:6][CH:7]=3)[N:17]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 143469694-(4-Pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester

Product 1

HCID 143469704-(4-(Pyridin-3-yl)pyrimidin-2-ylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 8 (19.6 g, 59.6 mmole) and 2N-sodium hydroxide (190 ml) were added to a reaction vessel under the solvent of water (190 ml) and ethanol (190 ml), mixed under reflux and cooled to RT, and pH thereof was adjusted to 1˜2 with hydrochloride solution. The mixture was mixed for 1 hr, and filtered to give the titled compound as yellow solid.

Workup

  1. additionmixed
  2. temperatureunder reflux
  3. additionThe mixture was mixed for 1 hr
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8c82f585d2f7478fbe681854b1c2d9de
Source dataset
uspto-grants-2009_03
Patent number
US07501424B2

Reaction notes

Loading…