1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10385550, compound

HRID 1356474Notes

Reaction equation

HRID 1356474 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)=[O:8])=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH2:50]>C1COCC1.O.C(N(CC)CC)C.C(#N)C>[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH:50][C:14]([C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:2][CH:3]=2)=[O:8])=[CH:18][CH:17]=1)=[O:15]

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 4590482HCID 4590482, compound

Product 1

HCID 10385550HCID 10385550, compoundYield 25.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(4-biphenylylcarbonylamino)benzoic acid (0.323 g) in THF (15 ml)/acetonitrile (15 ml) were added WSC (0.248 g), HOBt (0.156 g), N,N-dimethylethylenediamine (0.097 g), and triethylamine (0.21 ml). After stirring at room temperature for 18 hr, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride sequentially, dried, and concentrated. The residue was recrystallized from methanol/diethyl ether to obtain the titled compound (0.100 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 10% aqueous potassium carbonate and saturated aqueous sodium chloride sequentially
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-f992392759f9421c9254a34c15317e6e
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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