Ethylamine → HCID 57665100, compound

HRID 1717247Notes

Reaction equation

HRID 1717247 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=O)[O:18]C(C)(C)C)=[CH:12][CH:11]=2)[N:8]=[N:7][C:6]=1[C:24]([NH:26][CH:27]1[CH2:29][CH2:28]1)=[O:25])[CH2:2][CH:3]=[CH2:4].FC(F)(F)C(O)=O.ClC(OC1C=C[C:44]([N+:47]([O-])=O)=[CH:43]C=1)=O.C(N)C>ClCCl.CN(C)C1C=CN=CC=1.O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([NH:47][CH2:44][CH3:43])=[O:18])=[CH:14][CH:15]=2)[N:8]=[N:7][C:6]=1[C:24]([NH:26][CH:27]1[CH2:29][CH2:28]1)=[O:25])[CH2:2][CH:3]=[CH2:4]

Participants

9

Reactant 4

HCID 6341EthylamineHCID 6422Trifluoroacetic acidHCID 821294-Nitrophenyl chloroformateHCID 57665117HCID 57665117, compound

Product 1

HCID 57665100HCID 57665100, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-{5-(3-buten-1-yl)-4-[(cyclopropylamino)carbonyl]-1H-1,2,3-triazol-1-yl}phenylcarbamate (1.58 g) obtained in Example 40d) in dichloromethane (20 ml) was added trifluoroacetic acid (5.0 ml). The reaction mixture was stirred at room temperature for 11 hr and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, and washed with 1M aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated to give a brown solid. A solution of the obtained solid residue and N,N-dimethylpyridin-4-amine (0.60 g) in dichloromethane (15 ml) was added dropwise to a solution of 4-nitrophenyl chloroformate (1.17 g) in dichloromethane (15 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 8 hr, and a solution (2M, 9.7 ml) of ethylamine in tetrahydrofuran was added. After further stirring for 1 hr, the reaction mixture was diluted with ethyl acetate, washed with 1M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=2/3 to ethyl acetate), and the resultant product was recrystallized from ethyl acetate/hexane to give the title compound as colorless crystals (1.03 g, 73%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with 1M aqueous sodium hydroxide solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customto give a brown solid
  7. temperaturecooling
  8. stirringThe reaction mixture was stirred at room temperature for 8 hr
  9. stirringAfter further stirring for 1 hr
  10. washwashed with 1M aqueous sodium hydroxide solution and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated
  13. customThe residue was purified by silica gel column (hexane/ethyl acetate=2/3 to ethyl acetate)
  14. customthe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-64f2a9fed07645f9b28637d231b92481
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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