[4-(4-[1,2,3]Triazol-1-yl-butyl)phenyl]-carbamic acid tert-butyl ester → [4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 1392238

Reaktionsgleichung

Reaktionsgleichung von HRID 1392238
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:25][C:26]1[N:27]=[C:28]([C:31]2[NH:32][C:33]3[C:38]([CH:39]=2)=[CH:37][C:36]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:35][CH:34]=3)[O:29][CH:30]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)[CH2:25][C:26]1[N:27]=[C:28]([C:31]2[NH:32][C:33]3[C:38]([CH:39]=2)=[CH:37][C:36]([O:40][C:41]([F:44])([F:42])[F:43])=[CH:35][CH:34]=3)[O:29][CH:30]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 69220256[4-(4-[1,2,3]Triazol-1-yl-butyl)phenyl]-carbamic acid tert-butyl esterHCID 1363319652-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole

Produkt 1

HCID 136331972[4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of [4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester (0.297 g, 0.94 mmol) in N,N-dimethyl formamide (5 ml) sodium hydride (0.050 g, 2.1 mmol) was added and the mixture stirred for 30 min at r.t. To this mixture a solution of 2-(4-chloromethyl-oxazol-2-yl)-5-trifluoromethoxy-1H-indole 0.3 g, 0.94 mmol) in N,N-dimethyl formamide (5 ml) was added and stirring continued for 16 h. The mixture was then poured on water (25 ml) and extracted with ethyl acetate (3×25 ml). The combined organic extracts was washed with water, brine and dried over sodium sulfate. After concentration in vacuo the crude product was purified on silica gel (iso-hexanes/ethyl acetate 1:2) to yield [4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-[2-(5-trifluoromethoxy-1H-indol-2-yl)-oxazol-4-ylmethyl]-carbamic acid tert-butyl ester as light yellow solid.

Aufarbeitung

  1. stirringstirring
  2. waitcontinued for 16 h
  3. additionThe mixture was then poured on water (25 ml)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe combined organic extracts was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentration in vacuo the crude product
  8. customwas purified on silica gel (iso-hexanes/ethyl acetate 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-5b5133160aae44da964fa3395110c878
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342030B2

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