Methanesulfonic Acid → 5-(2-Chloro-phenoxy)-2-pyrazin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13301노트

반응식

HRID 13301 반응식
CO[C:3]([C:5]1[CH:10]=[N:9][CH:8]=[CH:7][N:6]=1)=[NH:4].CS(O)(=O)=O.[Cl:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[O:19][C:20]1[CH:21]=[C:22](N)[C:23]([NH2:37])=[CH:24][C:25]=1[O:26][C:27]1[CH:28]=[N:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=1>CN1CCCC1=O>[Cl:16][C:17]1[CH:42]=[CH:41][CH:40]=[CH:39][C:18]=1[O:19][C:20]1[C:25]([O:26][C:27]2[CH:28]=[N:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=2)=[CH:24][C:23]2[NH:37][C:3]([C:5]3[CH:10]=[N:9][CH:8]=[CH:7][N:6]=3)=[N:4][C:22]=2[CH:21]=1

참가 물질

5

반응물 3

HCID 6395Methanesulfonic AcidHCID 470894Methyl pyrazine-2-carboximidateHCID 231454214-(2-Chlorophenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

생성물 1

HCID 231451595-(2-Chloro-phenoxy)-2-pyrazin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

15 mg of methylpyrazin-2-imidate (pyrazine-2-carboximidic acid methyl ester) and 0.0065 ml of methanesulfonic acid were added to an N-methylpyrrolidinone (0.5 ml) solution of 38 mg of 4-(2-chloro-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in Example 204 (step 1), and the reaction liquid was stirred at 120° C. for 20 minutes. The reaction liquid was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and then dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a yellow solid.

후처리

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. customwas purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  4. additionThe solvent of the resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-949f26eae5ff4e1cbbe56e7cc0d3080e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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