Potassium sodium tartarate → HCID 9796757, compound

HRID 1166166Notes

Reaction equation

HRID 1166166 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([C:20](OCC)=[O:21])=[C:13]([C:15](OCC)=[O:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.COCCO[AlH2-]OCCOC.[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH2:20][OH:21])=[C:13]([CH2:15][OH:16])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 16684438Red-AlHCID 22997464HCID 22997464, compound

Product 1

HCID 9796757HCID 9796757, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To an ice cooled solution of diethyl 8-(2,6-dimethylbenzylamino)imidazo[1,2-a]pyridine-2,3-dicarboxylate (2.5 g, 6.3 mmol) in toluene (100 ml) was added Red-Al (14 ml, 45 mmol)(65% in toluene) during 3 h. The temperature was allowed to rise to room temperature and a Rochell salt solution (35 g potassium sodium tartrate in 250 ml H2O) was added. The organic layer was separated dried and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using dichloromethane: isopropylalcohol (4:1) gave 0.09 g (5%) of de desired product.

Workup

  1. customto rise to room temperature
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-fb33d7373285425bbf7d87cb1cfeadf2
Source dataset
uspto-grants-2003_09
Patent number
US06613775B1

Reaction notes

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