Ammonium Hydroxide → N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide

HRID 2085535Notes

Reaction equation

HRID 2085535 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:23][C:24]([NH:27][C:28](=[O:30])[CH3:29])([CH3:26])[CH3:25])[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9](OC3C=CC=CC=3)[C:8]=2[N:22]=1)[CH3:2].C([O-])(=O)C.[NH4+:35].[NH4+].[OH-]>O>[NH4+:6].[OH-:3].[NH2:35][C:9]1[C:8]2[N:22]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:23][C:24]([NH:27][C:28](=[O:30])[CH3:29])([CH3:25])[CH3:26])[C:7]=2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 21973845HCID 21973845, compound

Product 2

HCID 14923Ammonium HydroxideHCID 10172089N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamideYield 146.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A pressure flask was charged with N-{2-[2-(ethoxymethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide (980 mg, 2.39 mmol) and ammonium acetate (1.25 g). The flask was sealed and heated to 160° C. The solids soon melted to give a viscous oil and heating was continued for 24 h. The reaction mixture was cooled and treated with H2O and NH4OH solution until pH reached ˜12. The mixture was then extracted with CHCl3 (3×). The combined organic portions were washed with brine, dried with Na2SO4 and concentrated. Column chromatography (SiO2, 5% MeOH/CHCl3 saturated with NH4OH) gave N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}acetamide (584 mg) as a tan foam. MS m/z 334 (M+H). 1H NMR (300 MHz, CDCl3) δ 5.57 (s, 1H), 4.92 (s, 2H), 4.77 (s, 2H), 4.71 (br s, 2H), 3.62 (q, J=7.0 Hz, 2H), 2.44 (s, 6H), 1.96 (s, 3H), 1.30 (s, 6H), 1.24 (t, J=7.0 Hz, 3H).

Workup

  1. customThe flask was sealed
  2. customto give a viscous oil
  3. temperatureheating
  4. temperatureThe reaction mixture was cooled
  5. extractionThe mixture was then extracted with CHCl3 (3×)
  6. washThe combined organic portions were washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6cac82527845481288e79b1c3b5c9747
Source dataset
uspto-grants-2004_04
Patent number
US06720422B2

Reaction notes

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