Chloroacetaldehyde → 9-[4-(benzyloxy)phenyl]-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

HRID 572177Notes

Reaction equation

HRID 572177 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]=[C:16]2[NH2:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:26][CH:27]=O.O>CC(N(C)C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]3[CH:26]=[CH:27][N:24]=[C:16]23)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 962WaterHCID 86704985HCID 86704985, compound

Product 1

HCID 867049879-[4-(benzyloxy)phenyl]-9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 3-[4-(benzyloxy)phenyl]-3H-imidazo[4,5-b]pyridin-2-amine (1.58 g) and 6.1 M aqueous chloroacetoaldehyde solution (1.64 mL) in DMA (20 mL) was stirred at 90° C. for 1.5 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from hexane/THF to give the title compound (0.665 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from hexane/THF

Sources & evidence

ORD record
ord-05e2684c5ef1466da20e3c968ac47854
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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