Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-ethoxypyridin-2-yl)phenyl)guanidine

HRID 1059934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059934
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=2)[NH2:13])[CH:5]=1)[CH3:2].[C:17]([O:21][C:22]([NH:24][C:25]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=S)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)CC)(C)C.[I-].C[N+]1C=CC=CC=1Cl>ClCCl.C(OCC)(=O)C>[C:31]([O:30][C:28]([NH:27][C:25]([NH:24][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])=[N:13][C:12]1[CH:14]=[CH:15][CH:16]=[C:10]([C:6]2[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][N:7]=2)[CH:11]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 5193990N,N'-Di-Boc-thioureaHCID 186676293-(4-Ethoxypyridin-2-yl)aniline

Produkt 1

HCID 136134137N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-ethoxypyridin-2-yl)phenyl)guanidineAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 3-(4-ethoxypyridin-2-yl)aniline (258 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (399 mg) and diisopropylethyl-amine (0.482 ml) in dichloromethane (12 ml) was added 1-methyl-2-chloropyridinium iodide (400 mg), and the mixture was stirred for 2 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=3:1) to give N,N′-bis(tert-butoxycarbonyl) -N″-(3-(4-ethoxypyridin-2-yl)phenyl)guanidine (389 mg).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-82ec263ef00f402ab054602c04183466
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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