Ammonia → HCID 24805168, compound

HRID 1690740Notes

Reaction equation

HRID 1690740 reaction equation
O[CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1.S([O-])([O-])(=O)=O.[Mg+2].[NH3:27]>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:19][C:9]1([CH3:20])[CH:8]([N:7]2[C:3]([C:2]#[N:27])=[CH:4][N:5]=[CH:6]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[O:10]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 577811224-(5-Hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Product 1

HCID 24805168HCID 24805168, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (1.0 g, 3.76 mmol) (Example 6d) in THF (30 mL) is added magnesium sulfate (4.79 g, 0.055 mol) and ammonia (2M isopropanol, 9 mL, 0.018 mol). Manganese dioxide (9 mL, 0.055 mol) is then added and the reaction mixture is stirred at room temperature for 48 h. Filtration through celite and concentration in vacuo affords a residue, which is purified by reverse-phase HPLC to give 3-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbonitrile; MS (ESI) m/z 268.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.33 (s, 3 H), 1.60 (s, 3 H), 5.87 (s, 1 H), 7.57 (d, J=7.6 Hz, 1 H), 7.67-7.78 (m, 1 H), 7.78-7.98 (m, 3 H), 8.28 (dd, J=7.7, 1.4 Hz, 1 H).

Workup

  1. filtrationFiltration
  2. concentrationthrough celite and concentration in vacuo
  3. customaffords a residue, which
  4. customis purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-3dd47bae82c04a598f91ea95bb0bf1c6
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

Loading…