Triethylamine → 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamide

HRID 381383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381383
C(N(CC)CC)C.[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][N:27]=3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[CH2:47][CH2:48][NH2:49]>C(Cl)Cl>[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([NH:49][CH2:48][CH2:47][C:43]4[S:42][CH:46]=[CH:45][CH:44]=4)=[O:32])=[CH:28][N:27]=3)=[O:25])[CH2:22][CH2:23]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:9])[CH3:10]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 116521ThiopheneethanamineHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

Produkt 1

HCID 183628556-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Triethylamine (0. 8 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid (2g) in methylene chloride (30 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (0. 7 ml) at 0° C.˜5° C., the mixture was stirred at 5° C for 1 hour. With the successive addition of triethylamine (0.9 ml) and 2-thiophenethylamine (0.75 g), the mixture was stirred at 5° C.˜10° C. for 2 hours. The solution was washed with an aqueous sodium bicarbonate and water. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid, so obtained, was recrystallized with ethanol and hexane to give a desired compound of 1.92 g (yield: 74%).

Aufarbeitung

  1. temperaturecooled
  2. stirringthe mixture was stirred at 5° C.˜10° C. for 2 hours
  3. washThe solution was washed with an aqueous sodium bicarbonate and water
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated residue was treated with ether for crystallization
  7. customThe solid, so obtained
  8. customwas recrystallized with ethanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-4884cd17793d419096a507e3e8d4d7b5
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306860B1

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