Dimethylformamide → N-(4-tert-Butylbenzyl)-2-(quinoxalin-6-yl)propanamide

HRID 1626865Notes

Reaction equation

HRID 1626865 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][C:11](=[O:22])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[CH:30]([CH:32]=O)=O>O>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][C:11](=[O:22])[CH:12]([C:14]2[CH:15]=[C:16]3[C:17](=[CH:18][CH:19]=2)[N:20]=[CH:32][CH:30]=[N:21]3)[CH3:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7860Glyoxal2×HCID 57742164N-(4-tert-Butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide

Product 1

HCID 25222518N-(4-tert-Butylbenzyl)-2-(quinoxalin-6-yl)propanamideYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the flask of N-(4-tert-butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide (81 mg, 0.249 mmol) was added glyoxal (4 mL, 40% in water soln.) at room temperature, and additionally added DMF (4 mL) because SM was not soluble in glyoxal sufficiently. The reaction mixture was refluxed for 2 hrs then cooled to room temperature. The mixture was diluted with H2O (25 mL) and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:1) as eluant. Brown solid (m.p. 53-55° C.). yield: 55.5%

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-1816474a58134379a9c215e1cdec16ed
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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