Ammonium Chloride → 2-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester

HRID 1810956

Reaktionsgleichung

Reaktionsgleichung von HRID 1810956
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[N:20]([CH2:24][C:25](O)=[O:26])[N:19]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH4+].[Cl-]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:25](=[O:26])[CH2:24][N:20]2[C:21]([CH3:23])=[CH:22][C:18]([CH3:17])=[N:19]2)[CH2:12][CH2:11]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 572875(3,5-Dimethyl-1H-pyrazol-1-yl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 10932975Methyl 2-(piperazin-1-yl)benzoate

Produkt 1

HCID 665997292-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a vial containing the 2-piperazin-1-yl-benzoic acid methyl ester (0.667 g, 3.03 mmol) is added a pre-mixed solution containing (3,5-dimethyl-pyrazol-1-yl)-acetic acid (0.428 g, 2.78 mmol) and carbonyl dimidazole (0.567 g, 3.50 mmol). The mixture is stirred overnight and then diluted with 200 mL of EtOAc followed by 200 mL of saturated NH4Cl. The organic phase is washed with 2×200 mL of H2O and 1×200 mL of brine, dried (MgSO4), filtered and concentrated to give 0.849 g of 2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester in 86% yield.

Aufarbeitung

  1. additionis added a pre-mixed solution
  2. washThe organic phase is washed with 2×200 mL of H2O and 1×200 mL of brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5dc9f5d4f3534a918efb13f11835813a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362249B2

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