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

HRID 456880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456880
[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-0d87f57b7eeb4ea286e83f8af4d7376c
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186742B2

Notizen zur Reaktion

Wird geladen…