Pyridine → HCID 86647270, compound

HRID 2098310Notes

Reaction equation

HRID 2098310 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9](=O)[CH2:10][CH3:11])[N:6]=[N:5][C:4]2=[C:13]([C:16]([NH2:18])=[O:17])[N:14]=[CH:15][N:3]12.[CH3:19][O:20][NH2:21].Cl.N1C=CC=CC=1>CCO.CCOC(C)=O.CC#N>[CH3:19][O:20][N:21]=[C:9]([CH2:10][CH3:11])[CH2:8][N:7]1[C:2](=[O:1])[N:3]2[CH:15]=[N:14][C:13]([C:16]([NH2:18])=[O:17])=[C:4]2[N:5]=[N:6]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 441288084-Oxo-3-(2-oxobutyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Product 1

HCID 86647270HCID 86647270, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Oxo-3-(2-oxo-butyl)-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (Compound QQ-001) (25 mg, 0.1 mmol), MeONH2.HCl (13 mg, 0.15 mmol) were dissolved in an EtOH; Pyridine solution (1:1-0.5 ml). The reaction mixture was stirred for 16 hours before being concentrated in vacuo to give a crude residue which was redissolved in EtOAc (2 ml) and MeCN (2 mL). The solution was washed with aqueous 1M HCl and then dried (MgSO4), filtered and concentrated in vacuo. The crude product was redissolved in MeCN and passed through a silica plug. The filtrate was concentrated in vacuo to give the desired product as a green solid (17 mg, 61%). 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.87 (1H, s), 8.86 (1H, s), 7.84 (2H, s), 7.71 (2H, s), 5.17 (2H, s), 5.04 (2H, s), 3.83 (2.85H, s), 3.73 (3H, s), 2.32 (2H, q, J=7.6 Hz), 2.19 (2H, q, J=7.2 Hz), 1.04 (3H, t, J=7.6 Hz), 0.99 (3H, t, J=7.2 Hz). m/z: 302.3 ((M+Na)+, 100), 280.4 (MH+).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customto give a crude residue which
  3. washThe solution was washed with aqueous 1M HCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was redissolved in MeCN
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-68bedf9514274fd8a3d9329e724a23df
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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