Aniline → 5-(2-chloro-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13300노트

반응식

HRID 13300 반응식
NC1C=CC=CC=1.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=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]([NH2:38])[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>CO>[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:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=3)=[N:38][C:22]=2[CH:21]=1

참가 물질

5

반응물 3

HCID 6115AnilineHCID 142732-PyridinecarboxaldehydeHCID 231454214-(2-Chlorophenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine

생성물 1

HCID 231452095-(2-chloro-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
60 °C

실험 절차

0.26 ml of 1 M methanol solution of aniline and pyridine-2-carboxaldehyde (1/1) was added to a methanol (1 ml) solution of 35 mg of 4-(2-chlorophenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in (step 1), and the reaction liquid was stirred overnight at 60° C. The solvent was evaporated away under reduced pressure, and the resulting residue 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 pale yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-cfd4994a6436484099cfea130e5ed997
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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