Dimethylformamide → Ethyl 3-{[(4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091246노트

반응식

HRID 2091246 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:20][C:21]1[CH:29]=[CH:28][C:24](C(O)=O)=[CH:23][CH:22]=1)[C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13].CNC[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].[CH3:64][N:65]([CH3:68])[CH:66]=[O:67]>C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:66]([N:65]([CH3:68])[CH2:64][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:67])=[CH:23][CH:22]=1)[C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13]

참가 물질

8

반응물 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667778864-{[5-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoic acid

생성물 1

HCID 66778459Ethyl 3-{[(4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}phenyl)carbonyl](methyl)amino}propanoate수율 89%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a mixture of 4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoic acid (400 mg) synthesized in Example A123(3), ethyl 3-(methylamino)propanoate (199 mg), 1-hydroxybenzotriazole monohydrate (233 mg), triethylamine (422 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (291 mg), and the mixture was stirred at room temperature for 2.5 days. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (40-80% ethyl acetate/hexane) to give the title object compound (460 mg, 89%) as a pale-yellow oil.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (40-80% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-96793e0cf123402a8dfd7c0e9ef02ff3
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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