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

HRID 42057Notes

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]([O:28][CH3:29])=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[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]([O:28][CH3:29])=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:21]=3)=[C:8]([CH:14]=2)[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

The solid residue obtained in step A was dissolved in 2.5 ml of ethanol and 0.180 ml of aqueous solution 2N NaOH were 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 0.025 g (yield 77%) 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-809ac7c483c042138138339ab910d6cd
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536165B2

Reaction notes

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