2-Bromoethanol → 3-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamide

HRID 251377

Reaktionsgleichung

Reaktionsgleichung von HRID 251377
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1.[Br:29][CH2:30][CH2:31]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O.[NH4+].[Cl-]>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:14][CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:31][CH2:30][Br:29])[CH:22]=1

Komponenten

7

Edukt 5

HCID 108982-BromoethanolHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112458363-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 580889463-{5-Amino-4-[3-(2-bromo-ethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methylbenzamideAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide (472 mg, 1.26 mmol) in THF (dry, 20 mL) at 0° C. was added of 2-bromoethanol (785 mg, 6.3 mmol), PPh3 (1.3g, 5.04 mmol) and diethyl azodicarboxylate (877 mg, 5.04 mmol) and the mixture was stirred at room temperature for 72 h. An aqueous solution of NH4Cl was added then the THF layer was isolated. The aqueous layer was extracted by EtOAc. The combined organic phase was washed by brine, purified by preparatory HPLC, to provide the product as a white solid (360 mg, 59%). HPLC (4 minute 10-90 gradient) tR 2.72 min; MS m/z 483.14/485.09 [M+H]+.

Aufarbeitung

  1. extractionThe aqueous layer was extracted by EtOAc
  2. washThe combined organic phase was washed by brine
  3. custompurified by preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-31e3b9135a27465598f7f8657f9d85c5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863314B2

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