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Water → 6-chloro-N5-cyclopropyl-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide

HRID 514261
ノート
印刷プレビュー

反応式

HRID 514261 の反応式
[Cl:1][C:2]1[C:3]([C:29]([NH:31][CH:32]2[CH2:34][CH2:33]2)=[O:30])=[CH:4][C:5]2[N:9]=[C:8]([C:10]([NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])=[O:11])[NH:7][C:6]=2[CH:28]=1.[H-].[Na+].I[CH2:38][CH3:39].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:29]([NH:31][CH:32]2[CH2:34][CH2:33]2)=[O:30])=[CH:4][C:5]2[N:9]([CH2:38][CH3:39])[C:8]([C:10]([NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=3)[C:14]([F:15])([F:16])[F:17])=[O:11])=[N:7][C:6]=2[CH:28]=1.[Cl:1][C:2]1[C:3]([C:29]([NH:31][CH:32]2[CH2:34][CH2:33]2)=[O:30])=[CH:4][C:5]2[N:9]=[C:8]([C:10]([NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=3)[C:14]([F:15])([F:16])[F:17])=[O:11])[N:7]([CH2:38][CH3:39])[C:6]=2[CH:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 867139816-chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide

生成物 2

HCID 867139825-chloro-N6-cyclopropyl-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,6-dicarboxamide収率 12%
HCID 86713983
6-chloro-N5-cyclopropyl-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide
収率 18%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

6-Chloro-N5-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide (0.1 g, 0.22 mmol) was dissolved under argon at 0° C. in N,N-dimethylformamide (2 ml). Sodium hydride (60%; 0.0082 g, 0.22 mmol) was added and the mixture was stirred while cooling with ice for 1 h. Subsequently, iodoethane (0.034 g, 0.22 mmol) was added dropwise. The reaction mixture was thawed while stirring within 16 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (4/1) and gave 0.012 g (12% of theory) of 5-chloro-N6-cyclopropyl-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,6-dicarboxamide and 0.018 g (18% of theory) of 6-chloro-N5-cyclopropyl-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-benzimidazole-2,5-dicarboxamide.

後処理

  1. temperaturewhile cooling with ice for 1 h
  2. stirringwhile stirring within 16 h
  3. customthe phases were separated
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was chromatographed with cyclohexane/ethyl acetate (4/1)

出典と根拠

ORDレコード
ord-0667cc94e98f4682800072af02b38372
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09107411B2

反応ノート

読み込み中…

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