Chloromalonaldehyde → 7-(4-Bromo-2-chlorophenylamino)-8-chloro-3-formyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

HRID 494725

反応式

HRID 494725 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([NH2:20])=[N:6][CH:5]=1.Cl[CH:23]([CH:26]=O)[CH:24]=[O:25]>>[CH3:1][O:2][C:3]([C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]2[N:6]([C:23]([CH:24]=[O:25])=[CH:26][N:20]=2)[CH:5]=1)=[O:21]

参加物

3

反応物 2

HCID 147646ChloromalonaldehydeHCID 59519500Methyl 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloronicotinate

生成物 1

HCID 865967817-(4-Bromo-2-chlorophenylamino)-8-chloro-3-formyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

反応条件

温度
80 °C

実験手順

A suspension of 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloro-nicotinic acid methyl ester (28) (1.06 g, 2.72 mmol) and 2-chloro-malonaldehyde (587 mg, 5.43 mmol) was heated to 80° C. for 45 minutes. The solution was allowed to cool to room temperature, and then washed with saturated aqueous NaHCO3, and brine. The organic layer was dried over NaSO4, filtered, concentrated in vacuo, and purified by column chromatography (20:1 methylene chloride/methanol) to give the desired product as a dark yellow solid. The solid was triturated with ethyl acetate and isolated by filtration to provide the desired product as a yellow solid (0.436 g, 36%). MS (APCI+) m/z 442, 444, 446 (M+; Cl, Br pattern) detected.

後処理

  1. temperatureto cool to room temperature
  2. washwashed with saturated aqueous NaHCO3, and brine
  3. dry with materialThe organic layer was dried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (20:1 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-094eb7b2c2f64d5382c61074ca708ba2
出典データセット
uspto-grants-2009_05
特許番号
US07538120B2

関連ノート

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