Methyl iodide → HCID 86691842, compound

HRID 1616228Notes

Reaction equation

HRID 1616228 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=3)=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23].[CH3:26]I>C1COCC1.CO>[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH:19]([CH3:26])[C:20]#[N:21])[CH:16]=[CH:17][CH:18]=3)=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 54761747HCID 54761747, compound

Product 1

HCID 86691842HCID 86691842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask, {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}acetonitrile (14-48) (45 mg, 0.14 mmol) was added and dissolved in THF (1.3 ml) under nitrogen and cooled to −78° C. 1 M Sodium bis(hexamethylsilyl)amide (0.18 ml, 0.18 mmol) was added slowly to the cooled solution, followed by Methyl iodide (25 mg, 0.18 mmol). The cooled solution was stirred for 30 minutes, allowed to warm to room temperature and stirred for 10 minutes. The reaction 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-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}propanenitrile (33-1), HRMS (M+H)+: observed=349.2032, calculated=349.2023 and 2-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl}-2-methylpropanenitrile (33-2); HRMS (M+H)+: observed=363.2186, calculated=363.2179.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 10 minutes
  3. custompassed through a syringe
  4. filtrationfilter
  5. customThe solution was purified
  6. customthe desired fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9b5b66ec64564d2f9cea14ec685971c2
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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