Dimethylformamide → 4-(6-Chloro-3-[3-(2-chloro-3-fluorophenyl)-ureido]-2-hydroxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2233153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233153
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([NH2:24])[C:18]=2[OH:25])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[C:28]([F:38])=[C:29]([CH:35]=[CH:36][CH:37]=1)C(N=[N+]=[N-])=O.C[N:40](C)[CH:41]=[O:42]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([NH:24][C:41]([NH:40][C:37]3[CH:36]=[CH:35][CH:29]=[C:28]([F:38])[C:27]=3[Cl:26])=[O:42])[C:18]=2[OH:25])(=[O:15])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 18373502HCID 18373502, VerbindungHCID 81266090HCID 81266090, Verbindung

Produkt 1

HCID 670770234-(6-Chloro-3-[3-(2-chloro-3-fluorophenyl)-ureido]-2-hydroxy-benzenesulfonyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1d (3.8 g, 9.7 mmol) and 3-chloro-2-fluorobenzoyl azide (1b) (2.9 g, 14.5 mmol) in 5 mL of N,N-dimethylformamide was stirred at room temperature for 18 h. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (20/80, v/v), gave 3.6 g (66%) of 1e. LC-MS (m/z) 562.8 (M+H).

Aufarbeitung

  1. washwashed with water
  2. customto give the crude material
  3. customPurification by column chromatography on silica gel
  4. washeluting with ethyl acetate/hexane (20/80

Quellen und Nachweise

ORD-Eintrag
ord-a38b303c68bd467c8b8c0d98e4329c3d
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709485B2

Notizen zur Reaktion

Wird geladen…