Chloroacetic anhydride → N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 405837

反応式

HRID 405837 の反応式
[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH3:23])=[C:9]([NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[CH:10]=1)[NH2:4].[Cl:24][CH2:25][C:26](OC(=O)CCl)=O>CN1CCCC1=O.O>[Cl:24][CH2:25][C:26]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH3:23])=[C:9]([NH:11][C:12]([C:14]3[N:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]4=[N:16][CH:15]=3)=[O:13])[CH:10]=2)[N:4]=1

参加物

5

反応物 2

HCID 10946Chloroacetic anhydrideHCID 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 86677445N-(5-(5-(chloromethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

A mixture of N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide 9 (500 mg, 1.62 mmol) and 2-chloroacetic anhydride (553 mg, 3.23 mmol) in anhydrous 1-methyl-2-pyrrolidinone (10 mL) was heated in the microwave at 110° C. for 12 minutes. The crude was diluted with water and extracted with ethyl acetate. The organic was washed with water/brine mixture and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography. MS m/z 368.08 (M+1)+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic was washed with water/brine mixture
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe crude product was purified by silica chromatography

出典と根拠

ORDレコード
ord-3fa0a85c1d5141e5a6e1c73da4977fbc
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

関連ノート

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