Dimethylformamide → HCID 178442099, compound

HRID 230823Notes

Reaction equation

HRID 230823 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:25].CN(C=O)C.[N-:34]=[N+:35]=[N-:36].[Na+].N(CC)(CC)CC.Cl>CCOC(C)=O>[CH2:13]([C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3](=[O:26])[C:2]([CH3:1])([CH3:27])[CH3:28])=[C:7]([CH3:25])[CH:8]=1)([C:17]1[CH:18]=[CH:19][C:20]([C:21]2[NH:36][N:35]=[N:34][N:22]=2)=[CH:23][CH:24]=1)[CH2:15][CH3:16])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 57763487HCID 57763487, compound

Product 1

HCID 178442099HCID 178442099, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzonitrile (0.50 g, 1.32 mmol), and DMF (5 mL) is added NaN3 (0.26 g, 3.95 mmol) and Et3N.HCl (0.54 g, 3.95 mmol). The slurry is heated at 110° C. overnight. The slurry is diluted with EtOAc (50 mL), washed with 1M HCl (40 mL) water (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (20%-40% [89% EtOAc: 10% MeOH: 1% ACOH] gradient) to furnish the title compound (0.37 g, 0.88 mmol, 66%).

Workup

  1. washwashed with 1M HCl (40 mL) water (40 mL), brine (40 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by ISCO (20%-40% [89% EtOAc: 10% MeOH: 1% ACOH] gradient)

Sources & evidence

ORD record
ord-eac82c183db54b2fbc0bae5541f864a2
Source dataset
uspto-grants-2009_07
Patent number
US07566803B2

Reaction notes

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