Water → HCID 22672592, compound

HRID 1369574Notes

Reaction equation

HRID 1369574 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])=[CH:8][C:7]([C:20](OCC)=[O:21])=[CH:6][N:5]2[C:25]=1[CH3:26].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:13]([CH3:19])=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:18])=[CH:8][C:7]([CH2:20][OH:21])=[CH:6][N:5]2[C:25]=1[CH3:26]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 9906451HCID 9906451, compound

Product 1

HCID 22672592HCID 22672592, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylate (1.2 g, 3.4 mmol) in tetrahydrofuran (30 ml) was added LiALH4 (0.7 g, 18.5 mmol) during 20 min. at 5° C. 0.7 ml of water was added dropwise, followed by 0.7 ml of 15% sodium hydroxide and then 2.1 ml of water. The solids were removed by filtration and washed thoroughly with methylene chloride: methanol (1:1). The filtrate and washings were combined and the solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (10:1) as eluent. Treating the residue with diethyl ether and filtration gave 0.7 g (67%) of the title compound.

Workup

  1. customThe solids were removed by filtration
  2. washwashed thoroughly with methylene chloride: methanol (1:1)
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. additionTreating the residue
  6. filtrationwith diethyl ether and filtration

Sources & evidence

ORD record
ord-6532beac8650413aaa3c525110c13bf1
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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