N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide → N-Hydroxy-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 570974

Reaktionsgleichung

Reaktionsgleichung von HRID 570974
C([O:8][NH:9][C:10]([C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH3:22])[N:18]=[N:17][C:16]=12)=[O:11])C1C=CC=CC=1>C(OCC)(=O)C.CN(C=O)C.[Pd]>[OH:8][NH:9][C:10]([C:12]1[N:13]=[CH:14][N:15]2[C:20](=[O:21])[N:19]([CH3:22])[N:18]=[N:17][C:16]=12)=[O:11]

Komponenten

4

Edukt 1

HCID 49869276N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Produkt 1

HCID 135985859N-Hydroxy-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 22989253N,N-dimethylformamide ethyl acetateLösungsmittel

Versuchsvorschrift

A solution of N-(benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (200 mg, 0.67 mmol) and 10% Pd/C (20 mg) in ethyl acetate:DMF (5:1) (36 mL) was put under an atmosphere of hydrogen for 3 days. The mixture was filtered through a pad of Celite™ and the filtrate was concentrated under vacuum. The residue was suspended in ethyl acetate and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether to give the pure title compound as a pale orange solid (35 mg, 25% yield). δH (DMSO-d6): 11.2 (1H, s), 9.18 (1H, s), 8.82 (1H, s), 3.86 (3H, s).

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite™
  2. concentrationthe filtrate was concentrated under vacuum
  3. filtrationthe precipitate was filtered
  4. washwashed successively with water, ethyl acetate and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3d74d080c0404d81b0bf1e51b7056b7c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024018B2

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