Potassium Iodide → 4-{4-[2-(2-Butylpyridinylamino)ethoxy]phenyl}butanoic acid

HRID 1881033노트

반응식

HRID 1881033 반응식
CO[C:3](=O)[CH2:4][CH2:5][CH2:6]C1C=CC(OCCBr)=CC=1.C(N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC.[I-].[K+].C[O:32][C:33](=[O:57])[CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][N:46](C(CC)C)C2C=CC=CN=2)=[CH:39][CH:38]=1.[OH-].[Na+]>O1CCCC1.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:3]([C:23]1[C:28]([NH:46][CH2:45][CH2:44][O:43][C:40]2[CH:39]=[CH:38][C:37]([CH2:36][CH2:35][CH2:34][C:33]([OH:57])=[O:32])=[CH:42][CH:41]=2)=[CH:27][CH:26]=[CH:25][N:24]=1)[CH2:4][CH2:5][CH3:6]

참가 물질

10

반응물 5

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 14322668N-Butyl-2-pyridinamine2회HCID 251578524-(4-(2-Bromoethoxy)phenyl)butanoic acid methyl esterHCID 672995864-{4-[2-(2-Butyl(pyridin-2-yl)amino)ethoxy]phenyl}butanoic acid methyl ester

생성물 1

HCID 672998564-{4-[2-(2-Butylpyridinylamino)ethoxy]phenyl}butanoic acid수율 11%

시약·촉매·용매 4

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

4-(4-(2-bromoethoxy)phenyl)butanoic acid methyl ester (3) (956 mg) from Step 3, and N-butylpyridine-2-amine (4) (1.4 g) from Step 4, were dissolved in tetrahydrofuran (6 mL), then triethylamine (0.88 mL) and potassium iodide (530 mg) were added, and refluxed overnight by heating. Ethyl acetate (100 mL) was added to the reaction solution, and the organic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=6:1) to give a mixture of 4-{4-[2-(2-butyl(pyridin-2-yl)amino)ethoxy]phenyl}butanoic acid methyl ester and N-butylpyridine-2-amine (4). This mixture was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL), 2N sodium hydroxide aqueous solution (1 mL) was added, then stirred overnight at room temperature. The reaction solution was concentrated with 2N hydrochloric acid (1.1 mL), then the residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=1:1) to give the above-identified compound (128 mg, yield 11%) as a colorless oil.

후처리

  1. temperaturerefluxed overnight
  2. temperatureby heating
  3. washthe organic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL)
  4. dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum concentration
  5. customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=6:1)
  6. customto give
  7. concentrationThe reaction solution was concentrated with 2N hydrochloric acid (1.1 mL)
  8. customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-b21391d705584a27b351a315529ba71c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318781B2

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