Water → HCID 178458534, compound

HRID 1644594

Reaction equation

HRID 1644594 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:29][CH:30]([CH3:32])[CH3:31])=[C:13]([C:15]2[NH:28][C:18]3=[N:19][CH:20]=[C:21]([C:23](OCC)=[O:24])[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:29][CH:30]([CH3:32])[CH3:31])=[C:13]([C:15]2[NH:28][C:18]3=[N:19][CH:20]=[C:21]([CH2:23][OH:24])[CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178469700HCID 178469700, compound

Product 1

HCID 178458534HCID 178458534, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine-6-carboxylate (0.36 g) in tetrahydrofuran (5 ml) was added lithium aluminum hydride (48 mg) under ice-cooling, and the reaction mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated. The obtained crude crystals were washed with diethyl ether to give the title compound (0.12 g, yield 37%) as colorless crystals. melting point 167-168(C. purity 98%. M+H: 390.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude crystals
  7. washwere washed with diethyl ether

Sources & evidence

ORD record
ord-bb555b111aa84975a8c649d9f9dd8040
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Linked notes

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