Sodium Hydroxide → 3-Carboethoxy-2,6-dimethyl-8-(2,6-diethylbenzylamino)imidazo[1,2-a]pyridine

HRID 1386090ノート

反応式

HRID 1386090 の反応式
[NH2:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:18]([C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH3:29])[C:21]=1[CH:22]=O)[CH3:19].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:13]([C:9]1[N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([NH:1][CH2:22][C:21]3[C:20]([CH2:18][CH3:19])=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:28][CH3:29])[C:3]2=[N:11][C:10]=1[CH3:12])([O:15][CH2:16][CH3:17])=[O:14]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 226725728-Amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine

生成物 1

HCID 217173543-Carboethoxy-2,6-dimethyl-8-(2,6-diethylbenzylamino)imidazo[1,2-a]pyridine

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

A stirred mixture of 8-amino-3-carboethoxy-2,6-dimethylimidazo[1,2-a]pyridine (2.02 g, 8.6 mmol), zinc(II)chloride (1.48 g, 10.8 mmol) and 2,6-diethylbenzaldehyde (2.17 g, 13.4 mmol) in 50 ml methanol was treated with sodium cyanoborohydride (0.65 g, 10.3 mmol) and was refluxed overnight. The mixture was allowed to cool and then poured over 80 ml 1M sodium hydroxide. The precipitate formed was filtrated and washed with water and then purified by column chromatography on silica gel with dichloromethane:methanol (95:5) as eluent. The yield was 2.1 g (64%) of the title compound.

後処理

  1. temperaturewas refluxed overnight
  2. temperatureto cool
  3. customThe precipitate formed
  4. filtrationwas filtrated
  5. washwashed with water
  6. custompurified by column chromatography on silica gel with dichloromethane:methanol (95:5) as eluent

出典と根拠

ORDレコード
ord-7dd9bd6a144a4002ba121fe791a1f5f3
出典データセット
uspto-grants-2001_07
特許番号
US06265415B1

反応ノート

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