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

HRID 1386090Notes

Reaction equation

HRID 1386090 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7dd9bd6a144a4002ba121fe791a1f5f3
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

Loading…