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

HRID 13300ノート

反応式

HRID 13300 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cfd4994a6436484099cfea130e5ed997
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

反応ノート

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