Methyl bromoacetate → (3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid methyl ester

HRID 1988378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988378
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[CH3:26][O:27][C:28](=[O:31])[CH2:29]Br>CN(C)C=O>[CH3:26][O:27][C:28](=[O:31])[CH2:29][N:22]1[C:23]([CH3:25])=[CH:24][C:20]([C:17]2[CH:18]=[CH:19][C:2]([Cl:1])=[C:3]([C:4](=[O:5])[NH:6][CH2:7][C:8]3([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:16]=2)=[N:21]1

Komponenten

4

Edukt 2

HCID 60984Methyl bromoacetateHCID 111875812-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide

Produkt 1

HCID 58818174(3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid methyl esterAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide (1.08 g, 3 mmol), 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,2,3-diazaphosphorine on polystyrene (2.0 g, 4.6 mmol) and bromo-acetic acid methyl ester (0.69 g, 4.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 h. The mixture was filtered and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate to afford the title compound (1.05 g). (3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7cc3b85c7a044caa8d4434e1ab0a1324
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553972B2

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