Pyridine → 2-(4-chlorophenyl)-N-methoxy-N-methyl-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxamide

HRID 1353011ノート

反応式

HRID 1353011 の反応式
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH:21]=[C:22]([C:24](O)=[O:25])[N:23]=2)=[CH:15][CH:14]=1.[CH3:37][NH:38][O:39][CH3:40].Cl.N1C=CC=CC=1>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=3)[CH:21]=[C:22]([C:24]([N:38]([O:39][CH3:40])[CH3:37])=[O:25])[N:23]=2)=[CH:15][CH:14]=1

参加物

7

反応物 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 117939602-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxylic acid

生成物 1

HCID 229982182-(4-chlorophenyl)-N-methoxy-N-methyl-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒3 回

反応条件

温度
0 °C

実験手順

Oxalyl chloride (0.34 g, 2.65 mmole) in 5 ml acetonitrile was added to 16 ml acetonitrile containing dimethylformamide (0.25 g, 3.46 mmole) cooled to 0° C. After 15 minutes, 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxylic acid from step 1 (1.0 g, 2.65 mmole) was added with 20 ml acetonitrile. After warming to room temperature N,0-dimethylhydroxylamine HCl (0.28 g, 2.92 mmole) and pyridine (0.42 g, 5.31 mmole) were added and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated to give an oily solid. The amide was purified by silica gel chromatography: Anal. Calc'd. C19H15N3O4SCl (419.89); C, 54.35; H. 4.32; N, 10 10.01. Found: C, 53.96; H, 4.30; N, 9.68.

後処理

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. customto give an oily solid
  4. customThe amide was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-a0b9f10f15f24a5d99270f80cf512128
出典データセット
uspto-grants-2007_05
特許番号
US07220770B2

反応ノート

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