Ammonium Acetate → HCID 178428415, compound

HRID 408549Notes

Reaction equation

HRID 408549 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.O[C:19]1[C:23]([CH3:25])([CH3:24])[NH:22][C:21](=[O:26])[CH:20]=1.C([O-])(=O)C.[NH4+:31]>C(O)(=O)C>[CH3:16][C:15]1[NH:31][C:19]2[C:23]([CH3:25])([CH3:24])[NH:22][C:21](=[O:26])[C:20]=2[CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 667254294-hydroxy-5,5-dimethyl-1,5-dihydro-2H-pyrrol-2-oneHCID 178467936HCID 178467936, compound

Product 1

HCID 178428415HCID 178428415, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 200 mg (0.888 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutanenitrile (Example 2A), 226 mg (0.888 mmol, approx. 50% purity) 4-hydroxy-5,5-dimethyl-1,5-dihydro-2H-pyrrol-2-one [K. Matsuo et al., Chem. Pharm. Bull. 1984, 32, 3724-3729] and 102 mg (1.332 mmol) ammonium acetate in acetic acid (4 ml) was stirred at 100° C. for 15 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified first by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) and then by preparative TLC (eluent: dichloromethane/methanol 10:1) to give 33 mg (11% of th.) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified first by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-27d280bf61cd4c2db159f8f46ec36947
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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