Reaktion #2363024

Reaktionsgleichung

rac-tert-butyl (1-amino-3-methylbutan-2-yl)carbamate

6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid

HATU

4-methylmorpholine

Water TFA

→

rac-tert-Butyl {1-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]-3-methylbutan-2-yl}carbamate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was purified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA)
2. 2
   EinengenThe product fractions were concentrated
3. 3
   Waschenwashed twice with saturated aqueous sodium bicarbonate solution
4. 4
   ExtraktionThe aqueous phase was extracted twice with dichloromethane
5. 5
   Trocknenthe combined organic phases were dried over sodium sulphate
6. 6
   Filtrationfiltered off
7. 7
   Einengenconcentrated

Vorschrift

200 mg (0.57 mmol) of 6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid Example 16A, 191 mg (0.60 mmol) of HATU and 0.19 ml (1.70 mmol) of 4-methylmorpholine in DMF (3.6 ml) were stirred at RT for 20 min. 126 mg (0.62 mmol) of rac-tert-butyl (1-amino-3-methylbutan-2-yl)carbamate were then added and the reaction mixture was stirred at RT overnight. Water/TFA were then added and the mixture was purified by preparative RP-HPLC (acetonitrile/water gradient with addition of 0.1% TFA). The product fractions were concentrated and the residue was taken up in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate, filtered off and concentrated. This gave 264 mg (87% of theory, purity 100%) of the target compound.

Quelle