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

HRID 1756790

反応式

HRID 1756790 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-769b42aab1084e97b859d74b202a31d3
出典データセット
uspto-grants-1995_08
特許番号
US05442060

関連ノート

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