N-Methyl dicyclohexylamine → 4-tert-Butyl 1-methyl 2-((7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methyl)succinate

HRID 2099830

Reaktionsgleichung

Reaktionsgleichung von HRID 2099830
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([O:15][CH3:16])=[O:14])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.C1(N(C)C2CCCCC2)CCCCC1.[CH3:39][Si:40]([CH2:43][CH2:44][O:45][CH2:46]Cl)([CH3:42])[CH3:41]>O1CCCC1>[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:46][O:45][CH2:44][CH2:43][Si:40]([CH3:42])([CH3:41])[CH3:39])[N:9]=2)[CH:5]=[C:4]([CH2:11][CH:12]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]([O:15][CH3:16])=[O:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 24210N-Methyl dicyclohexylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 577947204-Tert-Butyl 1-methyl 2-((7-methyl-1H-indazol-5-yl)methyl)succinate

Produkt 1

HCID 690729894-tert-Butyl 1-methyl 2-((7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)methyl)succinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-tert-butyl 1-methyl 2-((7-methyl-1H-indazol-5-yl)methyl)succinate (0.6053 g, 1.82 mmol) and N-cyclohexyl-N-methylcyclohexanamine (0.4686 mL, 2.19 mmol) in tetrahydrofuran (10 mL) was added trimethylsilylethoxymethyl chloride (0.3859 mL, 2.19 mmol) at room temperature under nitrogen. The reaction was stirred overnight and the solvent was removed in vacuo. The crude product was taken up in ethyl acetate (10 mL) and washed with water (3×5 mL). The ethyl acetate layer was dried, filtered and concentrated. The final product was obtained by flash chromatography, eluting with 0% to 20% ethyl acetate/hexane. (0.5873 g, 70%) HPLC tR=1.89 min, MS(ESI)[M+H]+=462.94.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. washwashed with water (3×5 mL)
  3. dry with materialThe ethyl acetate layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0ef70621c5d8428ba9a0501e688a9681
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569578B2

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