1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 16222146, compound

HRID 1717428Notes

Reaction equation

HRID 1717428 reaction equation
[CH:1](/[C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[O:16])=[CH:11][CH:10]=2)[N:7]=[N:6][C:5]=1[C:23](O)=[O:24])=[CH:2]\[CH3:3].[CH:26]1([NH2:29])[CH2:28][CH2:27]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:26]1([NH:29][C:23]([C:5]2[N:6]=[N:7][N:8]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][C:19]([F:20])([F:21])[F:22])=[O:16])=[CH:11][CH:10]=3)[C:4]=2/[CH:1]=[CH:2]/[CH3:3])=[O:24])[CH2:28][CH2:27]1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68515283HCID 68515283, compound

Product 1

HCID 16222146HCID 16222146, compoundYield 52%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(1E)-prop-1-en-1-yl]-1-(4-{[(2,2,2-trifluoroethyl)amino]carbonyl}phenyl)-1H-1,2,3-triazole-4-carboxylic acid (1.96 g) obtained in Example 1215a) in DMF (22 ml) were successively added cyclopropylamine (0.46 ml), triethylamine (0.92 ml), HOBt (1.01 g) and WSC (1.27 g), and the reaction mixture was stirred at room temperature for 2.5 hr. Water and ethyl acetate were added to the reaction mixture 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) and recrystallized from ethyl acetate-diisopropyl ether to give the title compound as a white powder (1.13 g, 52%).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-d8153be25fdb4657a77f0ee94e6ac9a4
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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