2-(2,6-Diethyl-4-methylphenyl)malonamide → HCID 86719923, compound

HRID 924607Notes

Reaction equation

HRID 924607 reaction equation
[CH3:1][O:2][N:3]1[CH2:9][CH2:8][NH:7][NH:6][CH2:5][CH2:4]1.[CH2:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][CH3:20])[C:13]=1[CH:21]([C:25](N)=[O:26])[C:22](N)=[O:23])[CH3:11]>ClCCCl>[CH2:10]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][CH3:20])[C:13]=1[CH:21]1[C:25](=[O:26])[N:6]2[CH2:5][CH2:4][N:3]([O:2][CH3:1])[CH2:9][CH2:8][N:7]2[C:22]1=[O:23])[CH3:11]

Participants

4

Reactant 2

HCID 120568112-(2,6-Diethyl-4-methylphenyl)malonamideHCID 86719914HCID 86719914, compound

Product 1

HCID 86719923HCID 86719923, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A degassed solution in a microwave vial of 5-methoxy-[1,2,5]triazepane (free base, 50 mg, 0.38 mmol) and 2-(2,6-diethyl-4-methyl-phenyl)-malonamide (95 mg, 0.38 mmol) in 1,2-dichloroethane (2.5 ml) under argon was irradiated with microwaves at 180° C. for 5 minutes. The solvent was evaporated, the residue dissolved in 5N aqueous sodium hydroxide, the aqueous layer extracted twice with ethyl acetate and the combined organic layers discarded. The aqueous alkaline phase was acidified with cooling to pH 2-3 by addition of a 4N HCl solution and the product thoroughly extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Yield: 20 mg of 8-(2,6-diethyl-4-methyl-phenyl)-3-methoxy-tetrahydro-pyrazolo[1,2-a][1,2,5]triazepine-7,9-dione (compound P2.3) as a tan solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in 5N aqueous sodium hydroxide
  3. extractionthe aqueous layer extracted twice with ethyl acetate
  4. temperaturewith cooling to pH 2-3 by addition of a 4N HCl solution
  5. extractionthe product thoroughly extracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1afb5a1f55db4094bf0f8a476208a7b0
Source dataset
uspto-grants-2016_03
Patent number
US09282743B2

Reaction notes

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