Diisopropylethylamine → N-(1-tert-Butoxycarbonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamide

HRID 1280685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280685
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH2:18][CH:14]([C:15](Cl)=[O:16])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:28]=[CH:29][C:22]=12.C(N(C(C)C)CC)(C)C>C(#N)C>[C:33]([O:32][C:30]([N:27]1[C:23]2=[N:24][CH:25]=[CH:26][C:21]([NH:20][C:15]([CH:14]3[CH2:18][CH2:19][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12][CH2:13]3)=[O:16])=[C:22]2[CH:29]=[CH:28]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 22393192tert-Butyl 4-amino-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Produkt 1

HCID 22393147N-(1-tert-Butoxycarbonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamideAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-Benzyloxycarbonylisonipecotyl chloride (5 g) was added to a solution of 4-amino-1-tert-butoxycarbonyl-1H-pyrrolo[2,3-b]pyridine (3 g) and diisopropylethyamine (2.16 g) in acetonitrile (40 ml) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water and extracted with chloroform. The residue obtained by water washing, drying and then concentration under reduced pressure was purified by silica gel column chromatography to give 6.3 g of N-(1-tert-butoxycarbonyl-1H-pyrrolo-[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamide.

Aufarbeitung

  1. extractionextracted with chloroform
  2. customThe residue obtained by water washing
  3. customdrying
  4. concentrationconcentration under reduced pressure
  5. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a0fdea88f644788b0258fca9125fe18
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451825B1

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