p-Toluenesulfonic acid → Sorafenib Tosylate

HRID 2094794

Reaktionsgleichung

Reaktionsgleichung von HRID 2094794
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>CC(C)=O>[S:39]([C:36]1[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=1)([OH:42])(=[O:41])=[O:40].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:30])[F:31]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 216239Sorafenib

Produkt 1

HCID 406563Sorafenib TosylateAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide (sorafenib base) (100 g, 0.2152 mol) was suspended in acetone (1000 ml) at ambient temperature. p-toluene sulfonic acid (50 g, 0.290 mol) was dissolved in acetone (500 ml) and this solution was charged to above reaction mass drop wise in 15 minutes. The obtained precipitate was stirred for 1-2 hours at ambient temperature, filtered and washed with acetone (500 ml). It was vacuum dried for 12 hours at 50° C. to afford 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide tosylate (Sorafenib Tosylate) (130 g).

Aufarbeitung

  1. additionthis solution was charged to above reaction mass drop wise in 15 minutes
  2. filtrationfiltered
  3. washwashed with acetone (500 ml)
  4. customdried for 12 hours at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-d9c6c366bff14031b2d9871a91e4536a
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445687B2

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