Water → HCID 21717366, compound

HRID 1386065Notes

Reaction equation

HRID 1386065 reaction equation
[C:1]([C:6]1[N:10]2[CH:11]=[C:12]([CH3:25])[CH:13]=[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:24])[C:9]2=[N:8][C:7]=1[CH3:26])(OCC)=[O:2].COCCO[AlH2-]OCCOC.[Na+].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].O>C1(C)C=CC=CC=1>[CH3:26][C:7]1[N:8]=[C:9]2[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:24])=[CH:13][C:12]([CH3:25])=[CH:11][N:10]2[C:6]=1[CH2:1][OH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 2724148Sodium potassium tartrate tetrahydrateHCID 16684438Red-AlHCID 21717328HCID 21717328, compound

Product 1

HCID 21717366HCID 21717366, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 3-carboethoxy-2,6-dimethyl-8-(2,6-dimethylbenzylamino)imidazo[1,2-a]pyridine (0.4 g, 1.1 mmol) in 10 ml toluene was cold with ice- water, Red-AL 65% in to toluene (2.1 g, 6.6 mmol) was added after 30 min. The solution was stirred for 2 h at room temperature. 10 ml of Rochelle-salt solution (sodium potassium tartrate tetrahydrate, 35 g/250 ml water) was added dropwise, 10 ml toluene was added, the organic layer was separated and washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluent dichloromethane:methanol 9:1, to give 0.21 g, (62%) of the title compound.

Workup

  1. additionwas added after 30 min
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel, eluent dichloromethane:methanol 9:1

Sources & evidence

ORD record
ord-4dfa35d364ed48749511375dc026f43c
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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