1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57665066, compound

HRID 1717341Notes

Reaction equation

HRID 1717341 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][C:10]=1[N:20]1[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][F:30])=[C:23]([C:31](O)=[O:32])[N:22]=[N:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34]1([NH2:37])[CH2:36][CH2:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(#N)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][C:10]=1[N:20]1[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][F:30])=[C:23]([C:31]([NH:37][CH:34]2[CH2:36][CH2:35]2)=[O:32])[N:22]=[N:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515702HCID 68515702, compound

Product 1

HCID 57665066HCID 57665066, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-{2-(benzyloxy)-4-[(ethylamino)carbonyl]phenyl}-5-(5-fluoropentyl)-1H-1,2,3-triazole-4-carboxylic acid (0.49 g) obtained in Example 137b) in acetonitrile (5 ml) were successively added cyclopropylamine (0.09 ml), triethylamine (0.18 ml), HOBt (0.20 g) and WSC (0.25 g), and the reaction mixture was stirred at room temperature for 3.5 hr, and then at 60° C. for 1 hr. After allowing the reaction mixture to cool, the solvent was evaporated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the residue, and the organic layer was separated. 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=1/1 to ethyl acetate) to give the title compound as a colorless amorphous substance (0.31 g, 59%).

Workup

  1. waitat 60° C. for 1 hr
  2. temperatureto cool
  3. customthe solvent was evaporated under reduced pressure
  4. additionA saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the residue
  5. customthe organic layer was separated
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-38d3b1f3cbb74619a0bb3acb6cb9faa5
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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