Hydrochloric Acid → 1-(4-Fluorophenyl)-2-((methyl(2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylic acid

HRID 2368486ノート

反応式

HRID 2368486 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][NH:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:31]I.Cl>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][N:19]([CH3:31])[C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71117752ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

生成物 1

HCID 711173991-(4-Fluorophenyl)-2-((methyl(2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate (23) (56 mg, 0.14 mmol) in DMF (2 mL) was added sodium hydride (60% in mineral oil, 7 mg, 0.28 mmol) and stirred for 30 minutes. To the solution was added methyl iodide (18 μL, 0.28 mmol) and again stirred overnight at room temperature. Ethyl acetate was added and the reaction was acidified with 2N HCl. The ethyl acetate was separated and the aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(4-fluorophenyl)-2-((methyl(2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylic acid (24).

後処理

  1. customThe ethyl acetate was separated
  2. extractionthe aqueous layer was extracted again with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-36dd11502a784c94a5533709063aeaf3
出典データセット
uspto-grants-2014_04
特許番号
US08703776B2

反応ノート

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