HCID 66831769, compound → HCID 135985849, compound

HRID 570958Notes

Reaction equation

HRID 570958 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:12]=[CH:13][N:14]2[C:19](=[O:20])[N:18]([CH3:21])[N:17]=[N:16][C:15]=12)=O>Cl>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:11]1[N:12]=[CH:13][N:14]2[C:19](=[O:20])[N:18]([CH3:21])[N:17]=[N:16][C:15]=12

Participants

3

Reactant 1

HCID 66831769HCID 66831769, compound

Product 1

HCID 135985849HCID 135985849, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(2-aminophenyl)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (300 mg) in 3N HCl (15 mL) was heated at 90° C. overnight. After cooling to room temperature, the mixture was concentrated to dryness under high vacuum and the residue was dissolved in MeCN:MeOH. Triethylamine (170 μL) was added to the solution and the crude product was absorbed on silica and purified by flash chromatography using DCM:MeOH (95:5) as eluent to give 8 mg of the pure title compound as a green solid (3% yield). δH (DMSO d6): 13.0 (1H, s), 8.99 (1H, s), 7.73-7.75 (1H, d, J=7.5), 7.56-7.58 (1H, d, J=7.5), 7.23-7.27 (2H, m), 3.90 (3H, s).

Workup

  1. concentrationthe mixture was concentrated to dryness under high vacuum
  2. dissolutionthe residue was dissolved in MeCN
  3. additionTriethylamine (170 μL) was added to the solution
  4. customthe crude product was absorbed on silica
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a455c188eda345e89549db10fe1af8dd
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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