Cyclopropanecarbonyl chloride → [2'-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4'-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

HRID 1625668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625668
Cl.[CH2:2]([O:4][C:5](=[O:34])[CH2:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=3)=[CH:17][C:16]=2[CH2:30][NH:31][CH2:32][CH3:33])[C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)[CH3:3].C(N(CC)C(C)C)(C)C.[CH:44]1([C:47](Cl)=[O:48])[CH2:46][CH2:45]1>ClCCl.O>[CH2:2]([O:4][C:5](=[O:34])[CH2:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([O:27][CH2:28][CH3:29])=[CH:25][CH:26]=3)=[CH:17][C:16]=2[CH2:30][N:31]([C:47]([CH:44]2[CH2:46][CH2:45]2)=[O:48])[CH2:32][CH3:33])[C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)[CH3:3]

Komponenten

6

Edukt 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 66958971[4'-(6-Ethoxy-pyridin-3-yl)-2'-ethylaminomethyl-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester hydrochloride

Produkt 1

HCID 58149167[2'-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4'-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To [4′-(6-ethoxy-pyridin-3-yl)-2′-ethylaminomethyl-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester hydrochloride (0.357 g, 0.736 mmol) and N,N-diisopropylethylamine (0.75 mL, 4.3 mmol) in dichloromethane (4 mL) was added cyclopropanecarbonyl chloride (0.074 mL, 0.814 mmol), and the reaction was stirred at room temperature. Once no starting material was seen by analytical LCMS, the mixture was diluted with dichloromethane and water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated, and the residue was purified by silica gel chromatography (ethyl acetate in hexanes gradient) to give the title compound.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel chromatography (ethyl acetate in hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-22270dadad8d4bc799ae58bd40f6ed58
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785393B2

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