Ethanamine, 2,2,2-trifluoro- → HCID 86629813, compound

HRID 1717385Notes

Reaction equation

HRID 1717385 reaction equation
[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[I:13])=[N+:2]=[N-:3].[F:14][C:15]([F:19])([F:18])[CH2:16][NH2:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[N:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:17][CH2:16][C:15]([F:19])([F:18])[F:14])=[O:10])=[CH:6][C:5]=1[I:13])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 151795044-Azido-3-iodobenzoic acid

Product 1

HCID 86629813HCID 86629813, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-azido-3-iodobenzoic acid (5.00 g, 17.3 mmol) obtained in Example 379a) in DMF (80 ml) were added sequentially 2,2,2-trifluoroethylamine (2.5 g), triethylamine (3.6 ml), HOBt (1.3 g) and WSC (5.0 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 pale-yellow solid (2.93 g, 46%).

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-09932c3e59fd4abab9aa6306b39c187b
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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