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

HRID 1386090노트

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HRID 1386090 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7dd9bd6a144a4002ba121fe791a1f5f3
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265415B1

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