Trimethyl orthoacetate → Benzoic acid, 4-[2-[4-(2-methoxyethyl)-1-piperazinyl]-4-thiazolyl]-

HRID 606570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606570
[CH3:1][O:2][C:3](OC)(OC)[CH3:4].[N:9]1([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[N:19]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C([BH3-])#N.[Na+]>Cl.C(#N)C.C([O-])(=O)C.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:12]1[CH2:13][CH2:14][N:9]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=3)[N:19]=2)[CH2:10][CH2:11]1

Komponenten

7

Edukt 3

HCID 15050Trimethyl orthoacetateHCID 5003444Sodium cyanoborohydrideHCID 670474804-[2-(Piperazin-1-yl)-1,3-thiazol-4-yl]benzoic acid

Produkt 1

HCID 11653147Benzoic acid, 4-[2-[4-(2-methoxyethyl)-1-piperazinyl]-4-thiazolyl]-Ausbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 517045Sodium AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-[4-(4-Carboxy-phenyl)-thiazol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (5.0 mmol) was dissolved in hydrochloric acid in dioxane (4N, 25 ml) and the reaction stirred at RT for 2 h. The reaction was concentrated in vacuo to yield 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid. Trimethoxyethane (6.5 mmol) was dissolved in aqueous hydrochloric acid (1N, 10 ml) and the reaction heated at 50° C. for 1.5 h. The reaction was allowed to cool to RT and was then added to a suspension of 4-(2-piperazin-1-yl-thiazol-4-yl)-benzoic acid (5.0 mmol) in acetonitrile (25 ml) and sodium acetate buffer (1N, pH 5.5, 10 ml). The reaction was stirred at RT for 1.5 h. Sodium cyanoborohydride (6.5 mol) was added and the reaction stirred at RT for 16 h. The reaction was concentrated in vacuo and the product purified by flash chromatography (silica gel, 10% methanol in dichloromethane) to give the title product as a colourless oil (0.9 g). m/z=348 (100% M+H) in MS ES+.

Aufarbeitung

  1. temperatureto cool to RT
  2. stirringthe reaction stirred at RT for 16 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe product purified by flash chromatography (silica gel, 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-185e9e6e50c5478fb233f0c9c0c1b0dc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915300B2

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