Reaktion #1783120

Reaktionsgleichung

2-(2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

4,5-dihydro-3-(piperidin-4-yl)-1H-benzo[d][1,3]diazepin-2(3H)-one

EDC

HOBt

→

3-(1-(2-((5S)-2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Ausbeute 22.8%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc (3×)
2. 2
   Trocknendried over Na2SO4
3. 3
   Einengenconcentrated to a brown oil
4. 4
   SonstigeCrude product was purified by ISCO flash chromatography on a 12 g Redisep column
5. 5
   Wascheneluting with 5-15% MeOH in CH2Cl2

Vorschrift

2-(2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (125.5 mg, 0.295 mmol), 4,5-dihydro-3-(piperidin-4-yl)-1H-benzo[d][1,3]diazepin-2(3H)-one (144.7 mg, 0.5900 mmol), EDC (113.1 mg, 0.5900 mmol), and HOBt (90.35 mg, 0.5900 mmol) in DMF (6 mL) were stirred at RT overnight. The mixture was transferred to a separatory funnel with water, extracted with EtOAc (3×), the organic layers were combined, dried over Na2SO4 and concentrated to a brown oil. Crude product was purified by ISCO flash chromatography on a 12 g Redisep column eluting with 5-15% MeOH in CH2Cl2. Obtained 44 mg of desired 3-(1-(2-((5S)-2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one.

Quelle