p-Toluenesulfonic acid → Sorafenib Tosylate

HRID 2094794

반응식

HRID 2094794 반응식
[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]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 216239Sorafenib

생성물 1

HCID 406563Sorafenib Tosylate수율 94.8%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-d9c6c366bff14031b2d9871a91e4536a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445687B2

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