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

HRID 494725

반응식

HRID 494725 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-094eb7b2c2f64d5382c61074ca708ba2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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