1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(4-Biphenylylmethoxy)-N-[2-(N,N-dimethylamino)ethyl]nicotinamide

HRID 1356469Notes

Reaction equation

HRID 1356469 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[C:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][N:16]=2)=[CH:9][CH:8]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(N(CC)CC)C.C1COCC1>[C:7]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[O:20])=[CH:17][N:16]=2)=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 178174806-(4-Biphenylylmethoxy)nicotinic Acid

Product 1

HCID 185083656-(4-Biphenylylmethoxy)-N-[2-(N,N-dimethylamino)ethyl]nicotinamideYield 72.3%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of N,N-dimethylethylenediamine (160 mg) in acetonitrile (5 ml)/THF (10 ml) were added 6-(4-biphenylylmethoxy)nicotinic acid (450 mg), WSC (340 mg), HOBt (230 mg), and triethylamine (0.7 ml) at room temperature. After stirring at room temperature for 12 hr, the reaction mixture was diluted with 10% aqueous potassium carbonates and extracted with ethyl acetate/THF. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent; THF) and recrystallized from ethyl acetate/diisopropyl ether to obtain the titled compound (400 mg).

Workup

  1. extractionextracted with ethyl acetate/THF
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (eluent; THF)
  6. customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-c827072e90d04ce1a1706c8ef7d59cc9
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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