1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 2-(4-(4'-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881727
[CH:1]1([C:5]([NH:7][NH:8][C:9](=S)[NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]45[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])([CH2:27][CH2:28]4)[O:25][CH2:24]5)=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH:1]1([C:5]2[O:6][C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])([CH2:27][CH2:28]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)=[N:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86700833Methyl 2-(4-(4'-(2-(cyclobutanecarbonyl) hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Produkt 1

HCID 86700834Methyl 2-(4-(4'-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a reaction vial containing methyl 2-(4-(4′-(2-(cyclobutanecarbonyl)hydrazinecarbothioamido) biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (300 mg, 0.59 mmol) was added DCM (6 ml) at room temperature. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (204 mg, 1.06 mmol) was added and the mixture was stirred at room temperature for overnight. The reaction mixture was purified directly via column chromatography affording the title compound as off-white solid after drying (252 mg, 90% yield). LC/MS, ESI-MS(+): 474.4, RT: 1.40 (Condition E).

Aufarbeitung

  1. customThe reaction mixture was purified directly via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-df603e5309844ee88e1574a173f87aa3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993619B2

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