Acetonitrile → N-[5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539757ノート

反応式

HRID 539757 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]([CH:17]=3)[NH2:16])[N:10]=2)[CH:7]=1.C(#N)C.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[C:15]([NH:16][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[CH:17]=3)[N:10]=2)[CH:7]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 575162705-(6-Chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline

生成物 1

HCID 67983654N-[5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide収率 54%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

A 20 mL vial is charged with 5-(6-chloroimidazo[1,2-a]pyridin-2-yl)-2-(trifluoromethyl)aniline (0.156 g, 0.5 mmol), acetonitrile (4.12 mL) and pyridine (0.081 mL). The mixture is added trimethylacetyl chloride (0.123 mL, 0.001 mol) and stirred for 20 min at 80° C. The solution is concentrated, taken into EtOAc (10 mL) and washed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M). Organics are dried, concentrated purified on silica (0-100% EtOAc in Hexanes) to give the title compound (106 mg, 54% yield). LCMS m/z=396.4 [M+H]+, tR=2.54 min. (compound same as Example 81)

後処理

  1. concentrationThe solution is concentrated
  2. washwashed once with HCl (10 mL, 1M) and NaOH (10 mL, 1M)
  3. customOrganics are dried
  4. concentrationconcentrated
  5. custompurified on silica (0-100% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-62f960e453e24034a49e762f45ecdbef
出典データセット
uspto-grants-2014_10
特許番号
US08871767B2

反応ノート

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