Ammonium Acetate → HCID 178428410, compound

HRID 408551Notes

Reaction equation

HRID 408551 reaction equation
[S:1]1(=[O:8])(=[O:7])[CH2:5][CH2:4][C:3](=O)[CH2:2]1.[CH3:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](/[CH:19]=[C:20](/[C:23](=O)[CH3:24])\[C:21]#[N:22])[CH:17]=2)[NH:12][N:11]=1.C([O-])(=O)C.[NH4+:30]>C(O)(=O)C>[CH3:24][C:23]1[NH:30][C:3]2[CH2:4][CH2:5][S:1](=[O:8])(=[O:7])[C:2]=2[CH:19]([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[CH3:9])[C:20]=1[C:21]#[N:22]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxideHCID 178467936HCID 178467936, compound

Product 1

HCID 178428410HCID 178428410, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

850 mg (6.336 mmol) dihydrothiophen-3(2H)-one-1,1-dioxide, 1.78 g (6.336 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A) and 586 mg (7.603 mmol) ammonium acetate in acetic acid (30 ml) were heated to reflux overnight. After cooling, the mixture was evaporated to dryness, and the residue was taken up in ethyl acetate and washed with water and brine. The organic layer was separated and dried over sodium sulfate. After filtration and evaporation to dryness, the remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 89 mg (4% of th.) of the title compound.

Workup

  1. temperatureto reflux overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness
  4. washwashed with water and brine
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration and evaporation to dryness
  8. customthe remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-f88c981ad8ac4ee18966994417f4a0b9
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

Loading…