Triethylamine → (R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-(4-ethoxycarbonyl-1-phenylpyrazole-5-yl) urea

HRID 1756790Notes

Reaction equation

HRID 1756790 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]=1[NH2:11])=[O:5])[CH3:2].[C:18](=O)(OC(Cl)(Cl)Cl)[O:19]C(Cl)(Cl)Cl.C(N(CC)CC)C.[CH2:37]1[O:45][C:44]2[C:39](=[C:40]([C@@H:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:47][NH2:48])[CH:41]=[CH:42][CH:43]=2)[O:38]1>C(Cl)Cl>[CH2:37]1[O:45][C:44]2[C:39](=[C:40]([C@@H:46]([CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:47][NH:48][C:18]([NH:11][C:10]3[N:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:8]=[CH:7][C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:19])[CH:41]=[CH:42][CH:43]=2)[O:38]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85270Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylateHCID 94429TriphosgeneHCID 10331642(R)-2-(2, 3-methylenedioxyphenyl) heptylamine

Product 1

HCID 53777275(R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-(4-ethoxycarbonyl-1-phenylpyrazole-5-yl) ureaYield 220.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1.16 g of 5-amino-1-phenylpyrazole-4-carboxylic acid ethyl ester and 10 ml of methylene chloride were dropwise added 0.53 g of bis (trichloromethyl) carbonate and 1.11 g of triethylamine in order with ice cooling and stirring, and the resultant mixture was refluxed with heating for 4 hours. The reaction mixture was allowed to cool to room temperature, mixed with a solution of 1.18 g of (r)-2-(2, 3-methylenedioxyphenyl) heptylamine in 3 ml of methylene chloride, stirred at room temperature for 2 hours and the solvent evaporated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and the solvent evaporated. The residue was chromatographed on a column of silica gel, eluting with ethyl acetate and n-hexane (2:5) to give 1.94 g of the titled compound as amorphous solid.

Workup

  1. temperaturewith heating for 4 hours
  2. stirringstirred at room temperature for 2 hours
  3. customthe solvent evaporated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent evaporated
  9. customThe residue was chromatographed on a column of silica gel
  10. washeluting with ethyl acetate and n-hexane (2:5)

Sources & evidence

ORD record
ord-769b42aab1084e97b859d74b202a31d3
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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