Ethanol → HCID 178470772, compound

HRID 2221039Notes

Reaction equation

HRID 2221039 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH2:10][C:11]#N.C([O-])(O)=[O:14].[Na+].[CH3:18][CH2:19][OH:20]>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH2:10][C:11]([O:20][CH2:19][CH3:18])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 178510881HCID 178510881, compound

Product 1

HCID 178470772HCID 178470772, compound

Conditions

Temperature
0 °C

Procedure

3H-Imidazo[4,5-b]pyridin-2-ylacetonitrile was suspended in EtOH, and gaseous HCl was bubbled through for 3 hours. The suspension initially dissolved, but a precipitate started forming almost immediately. The reaction mixture was cooled to 0° C. and a cold saturated NaHCO3 solution was carefully added. Solid NaHCO3 was also added until a pH of 7.6 was achieved. The aqueous phase was then extracted with EtOAc, and the organic extracts were dried (Na2SO4). After evaporation of the solvent under reduced pressure, the residue was purified by chromatography on silica gel (10% MeOH in CH2Cl2 with 1% Et3N) providing the desired product as a light brown solid. LC/MS m/z 206.1 (MH+), Rt 0.97 minutes.

Workup

  1. customgaseous HCl was bubbled through for 3 hours
  2. dissolutionThe suspension initially dissolved
  3. customa precipitate started forming almost immediately
  4. extractionThe aqueous phase was then extracted with EtOAc
  5. dry with materialthe organic extracts were dried (Na2SO4)
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe residue was purified by chromatography on silica gel (10% MeOH in CH2Cl2 with 1% Et3N)

Sources & evidence

ORD record
ord-8d9c6d4ddeb8492e9b3aaac451a5464e
Source dataset
uspto-grants-2008_05
Patent number
US07368459B2

Reaction notes

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