Sodium Hydroxide → 4-{[4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1929201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929201
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[C:12]([C:18]([OH:20])=O)[NH:13]3)[N:6]=1.CC[N:23](C(C)C)C(C)C.[C:30]([O:34][C:35](=[O:43])NC1CCNCC1)([CH3:33])([CH3:32])[CH3:31].C1CN([P+](ON2N=[N:68][C:63]3[CH:64]=[CH:65][CH:66]=[CH:67]C2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:30]([O:34][C:35]([N:68]1[CH2:63][CH2:64][CH:65]([NH:23][C:18]([C:12]2[NH:13][C:14]3[C:10]([CH:11]=2)=[C:9]([O:8][CH2:7][C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)[CH:17]=[CH:16][CH:15]=3)=[O:20])[CH2:66][CH2:67]1)=[O:43])([CH3:33])([CH3:32])[CH3:31]

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 2724699PyBOPHCID 668416854-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

Produkt 1

HCID 668415664-{[4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid (170) (1.21 g, 4.2 mmol) is dissolved in 10 ml of DMF and the solution is cooled to 0° C. After addition of Huenigs base (2.16 ml, 12.6 mmol), piperidin-4-yl-carbamic acid tert-butyl ester (3) (841 mg, 4.2 mmol) and PyBOP (2.4 g, 4.6 mmol) the mixture is stirred at room temperature for 18 h. Ethyl acetate is added followed by concentrated sodium hydroxide, until a pH of 11 is reached. The organic layer is washed with brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product is purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1).

Aufarbeitung

  1. washThe organic layer is washed with brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe crude product is purified by flash-chromatography (silica gel, ethyl acetate/cyclohexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3fe28e42720443f3ae42738666b695f2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183366B2

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