Ammonium Acetate → HCID 178437991, compound

HRID 408546Notes

Reaction equation

HRID 408546 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](/[CH:12]=[C:13](/[C:16](=O)[CH3:17])\[C:14]#[N:15])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[O:19]1[CH2:23][C:22](=O)[CH2:21][C:20]1=[O:25].C([O-])(=O)C.[NH4+:30]>>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]3[C:13]([C:14]#[N:15])=[C:16]([CH3:17])[NH:30][C:22]4[CH2:23][O:19][C:20](=[O:25])[C:21]3=4)[CH:10]=2)[NH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 517165Ammonium AcetateHCID 521261Tetronic acidHCID 178437998HCID 178437998, compound

Product 1

HCID 178437991HCID 178437991, compound

Procedure

The title compound was prepared from 600 mg (2.508 mmol) (2E)-2-[(3-ethyl-1H-indazol-5-yl)-methylidene]-3-oxobutanenitrile (Example 7A), 256 mg (2.508 mmol) furan-2,4(3H,5H)-dione and 232 mg (3.010 mmol) ammonium acetate in analogy to the procedure described in Example 1 yielding 98 mg (12% of th.) of the racemic compound after purification by flash chromatography (silica gel; dichloromethane/methanol gradient, final mixture 30:1 v/v).

Workup

  1. customafter purification by flash chromatography (silica gel; dichloromethane/methanol gradient, final mixture 30:1 v/v)

Sources & evidence

ORD record
ord-64d0c3237f5d480a922c36479a6f0656
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

Loading…