Ammonia → 2-(3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1, 2, 3, 5]tetrazin-8-yl)thiazole-4-carboxamide

HRID 570929Notes

Reaction equation

HRID 570929 reaction equation
[NH:1]=[C:2]([C:10]1[N:11]=[CH:12][N:13]2[C:18](=[O:19])[N:17]([CH3:20])[N:16]=[N:15][C:14]=12)[S:3][CH2:4][C:5](=O)[C:6](O)=[O:7].ClC(OCC(C)C)=O.C([N:31](CC)CC)C.N>C1COCC1>[CH3:20][N:17]1[C:18](=[O:19])[N:13]2[CH:12]=[N:11][C:10]([C:2]3[S:3][CH:4]=[C:5]([C:6]([NH2:31])=[O:7])[N:1]=3)=[C:14]2[N:15]=[N:16]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 668316143-(Imino(3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)methylthio)-2-oxopropanoic acid

Product 1

HCID 498702482-(3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1, 2, 3, 5]tetrazin-8-yl)thiazole-4-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(imino(3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)methylthio)-2-oxopropanoic acid (0.700 g; 2.5 mmol) in dry THF (30 mL) under nitrogen was added isobutyl chloroformate (0.50 mL; 3.8 mmol), followed by triethylamine (0.53 mL; 3.8 mmol). The mixture was stirred for 1 hour, and then ammonia solution (0.5 M in dioxane; 20 mL) was added, and stirring continued for a further 3 hours. The precipitate was filtered, washed with water (5×20 mL) and diethyl ether (2×15 mL) to yield the title compound as a pale yellow solid (0.223 g; 40%). δH (DMSO-d6) 8.94 (1H, s), 8.42 (1H, s), 7.74 (1H, bs), 7.59 (1H, bs), 3.89 (3H, s).

Workup

  1. stirringstirring
  2. waitcontinued for a further 3 hours
  3. filtrationThe precipitate was filtered
  4. washwashed with water (5×20 mL) and diethyl ether (2×15 mL)

Sources & evidence

ORD record
ord-d53ec5c6b3e5437f99f1120e3068f949
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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