Trifluoroacetic acid → 2-[(3-chloro-4-hydroxybenzoyl)(methyl)amino]-N-isopropyl-5-phenoxybenzamide

HRID 2099980

Reaktionsgleichung

Reaktionsgleichung von HRID 2099980
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[O:31]CC1C=CC(OC)=C(OC)C=1)[C:5]([N:7]([CH3:27])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][C:9]=1[C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[O:6].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[OH:31])[C:5]([N:7]([CH3:27])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:10][C:9]=1[C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[O:6]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 577968883-chloro-4-[(3,4-dimethoxyphenyl)methoxy]-N-methyl-N-[2-[[(1-methylethyl)amino]carbonyl]-4-phenoxyphenyl]-benzamide

Produkt 1

HCID 114958652-[(3-chloro-4-hydroxybenzoyl)(methyl)amino]-N-isopropyl-5-phenoxybenzamideAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 44C (30 mg, 0.05 mmol) in CH2Cl2 (1 mL) at 0° C. was treated with TFA (0.05 mL). The solution was warmed to room temperature and stirred for 16 hours. The crude mixture was purified by chromatography (SiO2, 50% EtOAc in hexane) to afford 44D (15 mg, 68%). HPLC Retention Time=3.09 min (YMC ODSA 5 u C18 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm) [M+H+]=439.

Aufarbeitung

  1. customThe crude mixture was purified by chromatography (SiO2, 50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cdace0df7fed4bf5b36840eb8386f000
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569725B2

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