Diisopropylethylamine → 4-(5-amino-6-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamide

HRID 2204832

Reaktionsgleichung

Reaktionsgleichung von HRID 2204832
CCN(C(C)C)C(C)C.[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:21]2[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][CH:22]=2)=[N:15][C:16]=1[C:17]([NH:19][NH2:20])=[O:18].Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[NH2:10][C:11]1[N:12]=[CH:13][C:14]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])=[CH:30][CH:31]=2)=[N:15][C:16]=1[C:17]1[O:18][C:33](=[O:35])[NH:20][N:19]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 594716414-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide

Produkt 1

HCID 594716354-(5-amino-6-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

DIPEA (86.08 mg, 116.0 μL, 0.6660 mmol) was added to a solution of 4-(5-amino-6-(hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide (100 mg, 0.3330 mmol) in DCM (6.500 mL) under nitrogen. A solution of triphosgene (39.53 mg, 0.1332 mmol) in DCM (100.0 μL) was then added dropwise to the stirred solution. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the solid obtained dried under vacuum to yield the product (106. g mg, 98% yield); 1H NMR (400.0 MHz, DMSO) d 2.96 (s, 3H), 3.00 (s, 3H), 7.33 (br s, 2H), 7.52 (d, 2H), 8.09 (d, 2H), 8.89 (s, 1H) and 12.98 (br s, 1H) ppm; MS (ES+) 327.12

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solid obtained
  3. customdried under vacuum
  4. customto yield the product (106. g mg, 98% yield)

Quellen und Nachweise

ORD-Eintrag
ord-a73ccef759dd427db57f49d8916ff56e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365557B2

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