1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664756, compound

HRID 1717381Notes

Reaction equation

HRID 1717381 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[C:15]([C:22](O)=[O:23])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH:25]1([NH2:28])[CH2:27][CH2:26]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[CH:25]1([NH:28][C:22]([C:15]2[N:14]=[N:13][N:12]([C:9]3[CH:10]=[CH:11][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=3)[C:16]=2[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[O:23])[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68517352HCID 68517352, compound

Product 1

HCID 57664756HCID 57664756, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-{4-[(ethylamino)carbonyl]phenyl}-5-(2-thienyl)-1H-1,2,3-triazole-4-carboxylic acid (764 mg) obtained in Example 336a) in DMF (5 ml) were sequentially added cyclopropylamine (0.23 ml), triethylamine (0.46 ml), HOBt (170 mg) and WSC (640 mg), 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=4/6 to ethyl acetate) and recrystallized from ethyl acetate to give the title compound as a colorless powder (543 mg, 64%).

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=4/6 to ethyl acetate)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9e4fc7797f5e4b95b00a9f8fb9bee651
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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