Tris(hydroxymethyl)aminomethane → N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

HRID 2101521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101521
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 62325Isobutyryl chlorideHCID 119510703-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine

Produkt 1

HCID 11951240N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Isobutyryl chloride (11 mg, 0.1 mmol) was added to a solution of 3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine (see Example 21) (30 mg, 0.09 mmol) in CH2Cl2 (1 mL). The reaction was shaken at room temperature. After 72 h, trisamine resin (79 mg, 0.1 mmol) was added and the reaction was shaken for another 4 h. The reaction was filtered and the resin was washed with CH2Cl2 (2 mL). The filtrates were combined and concentrated in vacuo. Preparative TLC (silica, 20:1 CH2Cl2:MeOH, Rf=0.4) provided N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide, 24a as a white solid (15 mg, 40%); MS m/z 418 [C21H21Cl2N3O2+H]+.

Aufarbeitung

  1. stirringthe reaction was shaken for another 4 h
  2. filtrationThe reaction was filtered
  3. washthe resin was washed with CH2Cl2 (2 mL)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7c7825d9b33d41ffa86333fdcfeff637
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572921B2

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