Trifluoroacetic acid → 4-(2-azetidin-3-yl-4-chlorophenoxy)-5-chloro-N-(5-chloro-1,3-thiazol-2-yl)-2-fluorobenzenesulfonamide

HRID 1692198

Reaktionsgleichung

Reaktionsgleichung von HRID 1692198
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:29])=[C:6]([S:8]([N:11]([C:23]2[S:24][C:25]([Cl:28])=[CH:26][N:27]=2)CC2C=CC(OC)=CC=2OC)(=[O:10])=[O:9])[CH:7]=1.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([OH:49])=[C:36]([CH:38]2[CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39]2)[CH:37]=1.FC(F)(F)C(O)=O>ClCCl>[NH:40]1[CH2:41][CH:38]([C:36]2[CH:37]=[C:32]([Cl:31])[CH:33]=[CH:34][C:35]=2[O:49][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([S:8]([NH:11][C:23]3[S:24][C:25]([Cl:28])=[CH:26][N:27]=3)(=[O:9])=[O:10])=[C:5]([F:29])[CH:4]=2)[CH2:39]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 59436608Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylateHCID 594366225-Chloro-N-(5-chloro-1,3-thiazol-2-yl)-N-(2,4-dimethoxybenzyl)-2,4-difluorobenzenesulfonamide

Produkt 1

HCID 468408154-(2-azetidin-3-yl-4-chlorophenoxy)-5-chloro-N-(5-chloro-1,3-thiazol-2-yl)-2-fluorobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Chloro-N-(5-chloro-1,3-thiazol-2-yl)-N-(2,4-dimethoxybenzyl)-2,4-difluorobenzenesulfonamide (Preparation 655) and tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate (Preparation 237) were stirred in dichloromethane (2 ml) and trifluoroacetic acid (1 ml) to prepare the title compound using Method F above but where the N,N-dimethylformamide was replaced with dimethyl sulphoxide. The crude product was concentrated in vacuo and purified by preparative HPLC to afford the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-0c3c562e47eb41b5b379cc8bff3b778c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153814B2

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