Ammonium Acetate → HCID 178428417, compound

HRID 1474455Notes

Reaction equation

HRID 1474455 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[C:12](/[C:15](=O)[CH3:16])\[C:13]#[N:14])[CH:9]=2)[NH:4][N:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][C:27]#[N:28])=[CH:21][CH:20]=1.C([O-])(=O)C.[NH4+:34]>C(O)C.C(O)(=O)C>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:34][C:15]([CH3:16])=[C:12]([C:13]#[N:14])[CH:11]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[NH:4][N:3]=[C:2]4[CH3:1])[C:26]=2[C:27]#[N:28])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 2783172p-FluorobenzoylacetonitrileHCID 178467936HCID 178467936, compound

Product 1

HCID 178428417HCID 178428417, compound

Reagents, catalysts & solvents 1

HCID 18476134Acetic acid ethanolSolvent

Procedure

A mixture of 200 mg (0.89 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A), 159 mg (0.98 mmol) 3-(4-fluorophenyl)-3-oxopropanenitrile and 205 mg (2.66 mmol) ammonium acetate in ethanol/acetic acid (4:1 v/v, 11 ml) was heated to reflux overnight. After cooling, the reaction mixture was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to afford 136 mg (41% of th.) of the racemic title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe reaction mixture was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-1f10152f8fac48f2a8816e75d680c90b
Source dataset
uspto-grants-2015_04
Patent number
US09018234B2

Reaction notes

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