Acetonitrile → N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamide

HRID 539748ノート

反応式

HRID 539748 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2=[N: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])=[CH:10][N:4]2[N:3]=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:7]=[CH:6][C:5]2[N:4]([CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:18]([F:19])([F:20])[F:21])=[C:15]([NH:16][C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[CH:17]=3)[N:8]=2)[N:3]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 62493Pivaloyl chlorideHCID 866678495-(6-Chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)aniline

生成物 1

HCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamide収率 93.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

A 40 mL vial is charged with 5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)aniline (0.531 g, 1.7 mmol), acetonitrile (14 mL), and pyridine (0.275 mL). The stirred mixture is added trimethylacetyl chloride (0.419 mL, 3.4 mmol) and heated for 20 min at 80° C. The reaction is concentrated, taken into EtOAc (25 mL), washed once with HCl (15 mL, 1M) then NaOH (15 mL, 1M). Organic is dried, concentrated and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (630 mg, 93% yield). LCMS (m/z)=397.4, 399.3 [M+H]+, tR=2.87 min. (compound same as Example 126)

後処理

  1. concentrationThe reaction is concentrated
  2. washwashed once with HCl (15 mL, 1M)
  3. customOrganic is dried
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-a2826f11a43c4283a9c4e83983b1743b
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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