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Triethylamine → N-[2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethyl]-2-pyridin-4-yl-acetamide

HRID 378979
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HRID 378979 반응식
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=O)=[CH:3][CH:2]=1.[CH2:11](N(CC)CC)C.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=[N:24][C:22]=2[CH:23]=1.[CH2:28]1[CH2:33]CC(N=C=NC2CCCCC2)C[CH2:29]1.[O:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>O>[CH:45]1([O:46][C:47]2[C:48]([O:43][CH3:11])=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:22][NH:24][C:8](=[O:10])[CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:44][CH2:33][CH2:28][CH2:29]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 312751,4-Dioxane2회HCID 342284-Pyridineacetic acidHCID 757711-Hydroxybenzotriazole

생성물 1

HCID 21697280N-[2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethyl]-2-pyridin-4-yl-acetamide수율 71%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A suspension under nitrogen of 4-pyridin-acetic acid (0.43 g, 2.48 mmoles) hydrochloride in dioxane (20 ml) was added with triethylamine (0.34 ml, 0.25 g, 2.48 mmoles) and heated in water-bath to 40° C. for 10 minutes, then cooled and added with HOBT (0.33 g, 2.48 mmoles) and DCC (0.51 g, 2.48 mmoles). After 45 minutes a solution of 2-(2-cyclopentyloxy-3-methoxy-phenyl)-ethylanine (0.53 g, 2.25 mmoles), obtained as described in example 3 then desalted, in dioxane (5 ml) was dropped therein. After 1 hour the formed solid was filtered and washed with dioxane, then dried, taken up in ethyl acetate, filtered and washed with aqueous NaHCO3, then with water. The mother liquor was anhydrified and dried to give an oil which was purified by flash chromatography (eluent: methylene chloride/methanol 99:1 to 93:7) to give 0.57 g of the title product (yield: 71%).

후처리

  1. temperaturecooled
  2. customobtained
  3. additionwas dropped
  4. filtrationAfter 1 hour the formed solid was filtered
  5. washwashed with dioxane
  6. customdried
  7. filtrationfiltered
  8. washwashed with aqueous NaHCO3
  9. customdried
  10. customto give an oil which
  11. customwas purified by flash chromatography (eluent: methylene chloride/methanol 99:1 to 93:7)

출처 및 근거

ORD 기록
ord-858604581c2645ffafcb50cbc00df785
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06297257B1

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