Reaktion #155862

Reaktionsgleichung

4-methylmorpholine

2-(1-(tert-butoxycarbonyl)piperidin-2-yl)acetic acid

1H-benzo[d][1,2,3]triazol-1-ol

3-(methylthio)-1-phenyl-1H-indazol-6-amine

EDC.HCl

→

tert-butyl 2-(2-(3-(methylthio)-1-phenyl-1H-indazol-6-ylamino)-2-oxoethyl)piperidine-1-carboxylate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 50-mL 3-necked round-bottom flask purged
2. 2
   Temperaturmaintained with an inert atmosphere of nitrogen
3. 3
   workup.STIRRINGThe resulting solution was stirred for an additional 2 h at 15° C
4. 4
   WaschenThe resulting mixture was washed with aq. sodium bicarbonate (1×8 mL) and brine (2×8 mL)
5. 5
   TrocknenThe resulting mixture was dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated under vacuum

Vorschrift

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-(1-(tert-butoxycarbonyl)piperidin-2-yl)acetic acid (0.47 mg), 1H-benzo[d][1,2,3]triazol-1-ol (300 mg, 1.96 mmol), EDC.HCl (370 mg, 1.94 mmol), 4-methylmorpholine (590 mg, 5.84 mmol, 2.98 equiv) in dichloromethane (3 mL). The resulting solution was stirred for 10 min at 15° C. A solution of 3-(methylthio)-1-phenyl-1H-indazol-6-amine (500 mg, 1.96 mmol, 1.00 equiv) in dichloromethane (3 mL) was added. The resulting solution was stirred for an additional 2 h at 15° C. The resulting mixture was washed with aq. sodium bicarbonate (1×8 mL) and brine (2×8 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10˜1:3) to yield tert-butyl 2-(2-(3-(methylthio)-1-phenyl-1H-indazol-6-ylamino)-2-oxoethyl)piperidine-1-carboxylate as a white solid. MS: 481 (MH+).

Quelle