Sodium Hydroxide → 5-Cyclopropyl-2-(5-methyl-6-phenylpyridin-3-ylamino)benzoic acid

HRID 42054Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([NH:15][C:16]3[CH:17]=[N:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:20]([CH3:22])[CH:21]=3)=[C:8]([CH:14]=2)[C:9]([O:11]CC)=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O.CO.N>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([NH:15][C:16]3[CH:17]=[N:18][C:19]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[C:20]([CH3:22])[CH:21]=3)=[C:8]([CH:14]=2)[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

The solid residue obtained in step A was dissolved in ethanol (5 ml) and aqueous solution 2N NaOH (0.67 ml) was added. The mixture was heated at 60° C. for 2 hours, the solvent was evaporated and the solid obtained was suspended in water. The pH was taken to 6.5 and extracted with CHCl3. The crude mixture was purified over a SCX cartridge eluting with MeOH/NH3 10:1 affording 0.070 g (yield 29%) of the expected product.

Workup

customthe solvent was evaporated
customthe solid obtained
extractionextracted with CHCl3
customThe crude mixture was purified over a SCX cartridge

Sources & evidence

ORD record: ord-e11359836efc46f7bb1616627374d8f2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536165B2

Reaction notes

Loading…