Aminoacetaldehyde dimethyl acetal → HCID 178495962, compound

HRID 570948Notes

Reaction equation

HRID 570948 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].I.[CH3:9][N:10]1[C:15](=[O:16])[N:14]2[CH:17]=[N:18][C:19]([C:20](SC)=[NH:21])=[C:13]2[N:12]=[N:11]1>C(#N)C>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][C:20]([C:19]1[N:18]=[CH:17][N:14]2[C:15](=[O:16])[N:10]([CH3:9])[N:11]=[N:12][C:13]=12)=[NH:21]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 66831606Methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide

Product 1

HCID 178495962HCID 178495962, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Aminoacetaldehyde dimethyl acetal (68 μL, 0.624 mmol) was added to a suspension of methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide (200 mg, 0.568 mmol) in acetonitrile (8 mL) and the mixture was stirred overnight. The precipitate, which formed during the reaction, was filtered and washed successively with water, acetonitrile, ethyl acetate and diethyl ether to give the title product as a bright yellow solid (92 mg, 58%). δH (DMSO-d6): 9.50 (3H, bs), 9.17 (1H, s), 4.69-4.71 (1H, t, J=5.3), 3.95 (3H, s), 3.70-3.72 (2H, d, J=5.3), 3.37 (6H, s).

Workup

  1. customThe precipitate, which formed during the reaction
  2. filtrationwas filtered
  3. washwashed successively with water, acetonitrile, ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-66df04925dea4c79a68676dc9f5d1a12
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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