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Sodium hydride → (Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

HRID 220399
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 220399
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:22][CH3:23])[C:11]([C:13]([N:15]([CH:19]3[CH2:21][CH2:20]3)[CH:16]3[CH2:18][CH2:17]3)=[O:14])=[CH:12][C:7]2=[C:6]2[N:24]([CH3:27])[CH:25]=[N:26][C:5]=12.[CH3:28][O:29][CH:30]([O:39][CH3:40])[C:31](=[O:38])[CH:32]=[C:33](SC)[S:34][CH3:35]>CN(C=O)C.C(OCC)(=O)C>[CH:16]1([N:15]([CH:19]2[CH2:21][CH2:20]2)[C:13]([C:11]2[N:10]([CH2:22][CH3:23])[C:8]3=[N:9][C:4]([NH:3]/[C:33](/[S:34][CH3:35])=[CH:32]/[C:31](=[O:38])[CH:30]([O:29][CH3:28])[O:39][CH3:40])=[C:5]4[N:26]=[CH:25][N:24]([CH3:27])[C:6]4=[C:7]3[CH:12]=2)=[O:14])[CH2:18][CH2:17]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 111603891,1-Dimethoxy-4,4-bis(methylsulfanyl)but-3-en-2-oneHCID 581805034-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Produkt 1

HCID 58180627(Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (142 mg, 3.55 mmol) was added to 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 400 mg, 1.182 mmol) in DMF (7 mL) at room temperature and the mixture stirred for 30 min, 1,1-dimethoxy-4,4-bis(methylthio)but-3-en-2-one (394 mg, 1.773 mmol) was added and stirring continued overnight. The reaction mixture was diluted with ethyl acetate and washed with water, 10% lithium chloride and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 2-5% methanol/dichloromethane). (Z)-N,N-Dicyclopropyl-4-(4,4-dimethoxy-1-(methylthio)-3-oxobut-1-enylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (484 mg, 0.944 mmol, 80% yield) was obtained as a yellow solid.

Aufarbeitung

  1. stirringstirring continued overnight
  2. washwashed with water, 10% lithium chloride and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel using
  7. washan automated ISCO system (80 g column, eluting with 2-5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e1d3ec3b736c4652b8f7f13a5fac34a9
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08202881B2

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