تفاعل #2462974

معادلة التفاعل

HATU

DIEA

4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

1-isopropyl-piperidine-4-ylamine-dihydrochloride

DIEA

→

3-[5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid methyl ester

المردود 40.6%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred over night after which it
2. 2
   تركيزwas concentrated
3. 3
   workup.ADDITIONThe residue was diluted with DCM
4. 4
   غسيلwashed with a saturated NaHCO3 solution and brine
5. 5
   تجفيفThe organic layer was dried over MgSO4
6. 6
   تركيزconcentrated

الإجراء التجريبي

263 mg of (1.17 mmol) 4-(2-methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid were dissolved in DMF (10 mL). 488.4 mg (1.28 mmol) of HATU and DIEA (224 μl) were added and the resulting mixture was stirred for 45 minutes at RT. A solution of 276.3 mg (1.28 mmol) of 1-isopropyl-piperidine-4-ylamine-dihydrochloride and 448 μl of DIEA was added. The reaction mixture was stirred over night after which it was concentrated. The residue was diluted with DCM and washed with a saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated. Preparative HPLC(CH3CN/H2O gradient+0.05% formic acid) gave pure 3-[5-(1-isopropyl-piperidin-4-ylcarbamoyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid methyl ester (166 mg) as a colorless amorphous material. MS (ESI+): m/e=351 [M+H]+.

المصدر