HCID 86691838, compound → HCID 86691840, compound

HRID 1616226Notes

Reaction equation

HRID 1616226 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:23])[C:5]1=[O:24].[CH3:27][Mg]Br>C1COCC1.CO>[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:20]=[C:19]([C@@H:21]([OH:22])[CH3:27])[CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:10][CH:11]=2)[N:6]([CH3:23])[C:5]1=[O:24]

Participants

5

Reactant 2

HCID 86691838HCID 86691838, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86691840HCID 86691840, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask, 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-formylbenzonitrile (30-1) (70 mg, 0.2 mmol) was added under nitrogen, dissolved in THF (1 mL), and cooled to −78° C. 3M methylmagnesium bromide (0.08 ml, 0.24 mmol) was added slowly to the cooled solution and allowed to stir for 30 minutes. The reaction was warmed to room temperature for 30 minutes until complete conversion over starting material. The mixture was diluted with methanol, and passed through a syringe filter. The solution was purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile) and the desired fractions were collected and concentrated to produce 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-[(1S)-1-hydroxyethyl]benzonitrile (30-2). HRMS (M+H)+: observed=365.1976, calculated=365.1972.

Workup

  1. temperatureThe reaction was warmed to room temperature for 30 minutes until complete conversion
  2. custompassed through a syringe
  3. filtrationfilter
  4. customThe solution was purified
  5. customthe desired fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e76a04a3ac6b477c85cb9bb41bd54f46
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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