1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664729, compound

HRID 1717388Notes

Reaction equation

HRID 1717388 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[O:9])[CH:5]=[CH:4][C:3]=1[N:16]1[CH:20]=[C:19]([C:21]([OH:23])=O)[N:18]=[N:17]1.[CH:24]1([NH2:27])[CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[CH:24]1([NH:27][C:21]([C:19]2[N:18]=[N:17][N:16]([C:3]3[CH:4]=[CH:5][C:6]([C:8]([NH:10][CH2:11][C:12]([F:14])([F:13])[F:15])=[O:9])=[CH:7][C:2]=3[I:1])[CH:20]=2)=[O:23])[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68516938HCID 68516938, compound

Product 1

HCID 57664729HCID 57664729, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(2-iodo-4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxylic acid (2.08 g, 4.73 mmol) obtained in Example 379d) in DMF (20 ml) were sequentially added cyclopropylamine (500 mg), triethylamine (1.0 ml), HOBt (360 mg) and WSC (1.4 g), and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/20 to 1/1) to give the title compound as a colorless powder (1.66 g, 73%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/20 to 1/1)

Sources & evidence

ORD record
ord-6df7ca3ba3cc4814b131f6ffdd86e957
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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