Реакция #41736

Уравнение реакции

pyridine-2-carboxylate

1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride

tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate

methanol

thiourea

trifluoroacetic acid

→

2-{[4-(dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridin-2-carboxylic acid

Растворители

tetrahydrofuran

methylene chloride

Условия реакции

Обработка

1. 1
   КонцентрированиеThe mixture was then concentrated and to it
2. 2
   workup.STIRRINGstirred at ambient temperature overnight
3. 3
   ДругоеResulting 4-(2-{[4-dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography

Методика

To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-(dimethylamino)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. The mixture was then concentrated and to it was added tetrahydrofuran and 1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride (2 eq) and stir at ambient temperature for 16 h. tert-butyl4-(2-{[4-dimethylamino)phenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate crashes out of the reaction mixture. To it in methylene chloride was added trifluoroacetic acid and stirred at ambient temperature overnight. Resulting 4-(2-{[4-dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=403.

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