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

HRID 378979Notes

Reaction equation

HRID 378979 reaction equation
[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

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 312751,4-Dioxane2×HCID 342284-Pyridineacetic acidHCID 757711-Hydroxybenzotriazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-858604581c2645ffafcb50cbc00df785
Source dataset
uspto-grants-2001_10
Patent number
US06297257B1

Reaction notes

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