1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10411283, compound

HRID 1991088Notes

Reaction equation

HRID 1991088 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1/[CH:12]=[CH:13]/[C:14]([OH:16])=O)(=[O:3])[CH3:2].[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH:25]([CH3:29])[CH2:24]2)=[CH:20][CH:19]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:6](/[CH:12]=[CH:13]/[C:14]([N:26]2[CH2:27][CH2:28][N:23]([CH2:22][C:21]3[CH:30]=[CH:31][C:18]([Cl:17])=[CH:19][CH:20]=3)[CH2:24][CH:25]2[CH3:29])=[O:16])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 60137954HCID 60137954, compoundHCID 68538268HCID 68538268, compound

Product 1

HCID 10411283HCID 10411283, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g (0.42 mmol) (E)-3-(2-Acetylamino-4-chloro-phenyl)-acrylic acid, 85 mg 1-(4-Chloro-benzyl)-3-methyl-piperazine (0.38 mmol), 87 mg EDCI (0.45 mmol) and 61 mg HOBt (0.45 mmol) were dissolved in 5 ml DMF. The reaction mixture was stirred overnight, then partitioned between ethylacetate and aq. sodiumbicarbonate solution. The organic phase was further washed with water and brine. Removal of the solvent gave a crude product which was further purified by prep. HPLC (Waters XT column, acetonitrile/water). 0.11 mg (0.24 mmol, 63%) of the title compound was obtained as an pale yellow solid.

Workup

  1. custompartitioned between ethylacetate and aq. sodiumbicarbonate solution
  2. washThe organic phase was further washed with water and brine
  3. customRemoval of the solvent
  4. customgave a crude product which
  5. customwas further purified by prep

Sources & evidence

ORD record
ord-7c5f9089110a4b3ba91cc674a4fbdaf3
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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