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Acetic Anhydride → N-{3-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-4-methoxyphenyl}acetamide

HRID 349731
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 349731
[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=[O:8])=[O:5].CN1CC[CH2:28][C:27]1=[O:31].C(OC(=O)C)(=O)C>O>[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:3]=1[C:4]([NH:6][C:7](=[O:8])[NH:9][C:10]1[CH:15]=[C:14]([NH:16][C:27](=[O:31])[CH3:28])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=[O:5]
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Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 13387N-methyl-2-pyrrolidoneHCID 115665791-(2-Chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea

Produkt 1

HCID 9887086N-{3-[3-(2-Chloro-4,5-difluorobenzoyl)ureido]-4-methoxyphenyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.10 g (0.3 mmol) of 1-(2-chloro-4,5-difluorobenzoyl)-3-(5-amino-2-methoxyphenyl)urea was admixed with 1 ml of N-methylpyrrolidone, 0.11 g (0.3 mmol) of acetic anhydride and stirred at room temperature for 2 hours. The mixture was diluted with 20 ml of H2O and extracted three times with 20 ml of ethyl acetate each time. The combined organic phase was washed with H2O, concentrated and dried. The crude product was purified by preparative HPLC (column: Waters Xterra™ MS C18, 5 μm, 30×100 mm, eluent: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B). 0.03 g of the desired product was obtained.

Aufarbeitung

  1. extractionextracted three times with 20 ml of ethyl acetate each time
  2. washThe combined organic phase was washed with H2O
  3. concentrationconcentrated
  4. customdried
  5. customThe crude product was purified by preparative HPLC (column
  6. waitWaters Xterra™ MS C18, 5 μm, 30×100 mm, eluent: A: H2O+0.2% trifluoroacetic acid, B: acetonitrile, gradient: 2.5 minutes 90% A/10% B to 17.5 minutes 10% A/90% B)

Quellen und Nachweise

ORD-Eintrag
ord-45feb3582698417a8dfc24969f13cb0c
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179941B2

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