Fmoc isothiocyanate → N-(4-Ethoxy-5-methylcarbamoylpyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea

HRID 249728

Reaktionsgleichung

Reaktionsgleichung von HRID 249728
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:6]([C:7]([NH:9][CH3:10])=[O:8])=[CH:5][N:4]=1.[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>O1CCOCC1.C(Cl)Cl>[CH2:14]([O:13][C:11]1[C:6]([C:7](=[O:8])[NH:9][CH3:10])=[CH:5][N:4]=[C:3]([CH2:2][NH:1][C:34]([NH:33][C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])=[S:35])[CH:12]=1)[CH3:15]

Komponenten

5

Edukt 2

HCID 4154759Fmoc isothiocyanateHCID 577912976-Aminomethyl-4-ethoxy-N-methylnicotinamide

Produkt 1

HCID 57791308N-(4-Ethoxy-5-methylcarbamoylpyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thioureaAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

500 mg (2.39 mmol) of 6-aminomethyl-4-ethoxy-N-methylnicotinamide (Example 12f) were dissolved in 25 ml of dioxane and treated at RT with 672.4 mg (2.39 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After one hour, the mixture was freed from the solvent and the residue was taken up in DCM. It was washed three times with aqueous LiCl solution and once with water. After drying with MgSO4, the mixture was concentrated and the crude product (875 mg) thus obtained was reacted further without further purification.

Aufarbeitung

  1. washIt was washed three times with aqueous LiCl solution
  2. dry with materialAfter drying with MgSO4
  3. concentrationthe mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2629fc5befd24b84a8d127c603379184
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863269B2

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