{1-Isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol → (4-amino-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol

HRID 2426366Notes

Reaction equation

HRID 2426366 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([NH:16]CC3C=CC(OC)=CC=3)[C:8]=2[N:7]=[C:6]1[CH2:26][OH:27])[CH:2]([CH3:4])[CH3:3]>FC(F)(F)C(O)=O>[NH2:16][C:9]1[C:8]2[N:7]=[C:6]([CH2:26][OH:27])[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:13]=2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=1

Participants

3

Reactant 1

HCID 67262962{1-Isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol

Product 1

HCID 24782597(4-amino-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanolYield 93.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

{1-Isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol (3.08 g, 8.36 mmol) was dissolved in trifluoroacetic acid (31 mL) and stirred at room temperature over night. The solvent was removed under reduced pressure and concentrated hydrochloric acid (5 mL) was added. The suspension was stirred for 2 hours, the solid was isolated by filtration and washed with water to give 1.95 g of (4-amino-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol as a tan powder.

Workup

  1. customThe solvent was removed under reduced pressure and concentrated hydrochloric acid (5 mL)
  2. additionwas added
  3. stirringThe suspension was stirred for 2 hours
  4. customthe solid was isolated by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-b5a9704242ba4a328ad495338f8a57ae
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

Loading…