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

Reaction equation

HRID 570974 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3d74d080c0404d81b0bf1e51b7056b7c
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Linked notes

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