Acetic Acid → 4-{[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525642

Reaktionsgleichung

Reaktionsgleichung von HRID 1525642
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Br[CH2:14][C:15]1[C:29]([F:30])=[CH:28][C:18]([C:19]([NH:21][S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[O:20])=[C:17]([F:31])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH2:14][C:15]2[C:29]([F:30])=[CH:28][C:18]([C:19]([NH:21][S:22]([N:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[O:20])=[C:17]([F:31])[CH:16]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 580424365-Chloro-6-isopropoxypyridin-3-OLHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

Produkt 1

HCID 716160194-{[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]methyl}-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5-chloro-6-isopropoxypyridin-3-ol (Preparation 6, 44 mg, 0.232 mmol), 4-(bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide (Preparation 1, 83 mg, 0.23 mmol) and potassium carbonate (64 mg, 0.47 mmol) in dimethyl sulfoxide (5 mL) was stirred at room temperature for 16 hours. The reaction mixture was diluted with water (20 mL) and acidified to ˜pH 4 using acetic acid (2 mL). The resulting precipitate was filtered, washed with water (20 mL) and dried to afford the title compound as a white solid (32 mg).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water (20 mL)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a284f27bbef3449894fcd3114f1fa3f0
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085517B2

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