Sodium Hydroxide → HCID 21913043, compound

HRID 1245938Notes

Reaction equation

HRID 1245938 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([O:13][CH2:14][CH2:15][N:16]1[C:24]2[CH:23]=[C:22]([CH3:25])[N:21]=[C:20](OC3C=CC=CC=3)[C:19]=2[N:18]=[C:17]1[CH2:33][O:34][CH2:35][CH3:36])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>O>[CH2:6]([O:13][CH2:14][CH2:15][N:16]1[C:24]2[CH:23]=[C:22]([CH3:25])[N:21]=[C:20]([NH2:5])[C:19]=2[N:18]=[C:17]1[CH2:33][O:34][CH2:35][CH3:36])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 21912878HCID 21912878, compound

Product 1

HCID 21913043HCID 21913043, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ammonium acetate (25 g, 0.32 mol) and 1-[2-(benzyloxy)ethyl]-2-(ethoxymethyl)-6-methyl-4-phenoxy-1H-imidazo[4,5-c]pyridine (2.5 g, 6.0 mmol) were heated at 150° C. in a sealed tube for 22 hours. The resulting solution was adjusted to pH 14 with the addition of 20% sodium hydroxide, and water (50 mL) was added. The mixture was stirred for several hours to provide a yellow precipitate, which was isolated by filtration. The precipitate (1.75 g) was recrystallized from a 50:50 mixture of hexane:ethyl acetate (29 mL/g), and the crystals were isolated by filtration and dried under vacuum for 23 hours at 60° C. to provide 1.05 g of 1-[2-(benzyloxy)ethyl]-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine as small white crystals, mp. 127–128° C.

Workup

  1. additionwas added
  2. customto provide a yellow precipitate
  3. customwhich was isolated by filtration
  4. customThe precipitate (1.75 g) was recrystallized from a 50:50 mixture of hexane
  5. customethyl acetate (29 mL/g), and the crystals were isolated by filtration
  6. customdried under vacuum for 23 hours at 60° C.

Sources & evidence

ORD record
ord-5f3536cd7b7f47179609d624d4f3541c
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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