Methane → 3-(2,2-Dimethyl-propyl)-5-(4-fluoro-phenylethyl)-3H-imidazo[4,5-b]pyridin-2-ylamine

HRID 730022Notes

Reaction equation

HRID 730022 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2=[N:9][C:10]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH2:22].C>CO>[CH3:1][C:2]([CH3:24])([CH3:23])[CH2:3][N:4]1[C:8]2=[N:9][C:10]([CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH2:22]

Participants

4

Reactant 2

HCID 297MethaneHCID 688980803-(2,2-dimethyl-propyl)-5-(4-fluoro-phenylethynyl)-3H-imidazo[4,5-b]pyridin-2-ylamine

Product 1

HCID 688682873-(2,2-Dimethyl-propyl)-5-(4-fluoro-phenylethyl)-3H-imidazo[4,5-b]pyridin-2-ylamineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add methanol (1,200 mL) to combined lots of 3-(2,2-dimethyl-propyl)-5-(4-fluoro-phenylethynyl)-3H-imidazo[4,5-b]pyridin-2-ylamine (37.30 g) and heat to reflux. Add activated charcoal (3.73 g, 10 wt %) and reflux for 1 h. Filter while slurry is hot, then add water (375 mL) to the filtrate with stirring at room temperature. Filter off solids, wash 2×100 mL water and dry under reduced pressure at 45-50° C. to provide 30.0 g (80%) of the desired compound.

Workup

  1. temperatureheat to reflux
  2. temperaturereflux for 1 h
  3. filtrationFilter while slurry
  4. filtrationFilter off solids
  5. washwash 2×100 mL water
  6. customdry under reduced pressure at 45-50° C.

Sources & evidence

ORD record
ord-ff809430d8d649a288107d8fd70877ab
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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