Ammonium Acetate → HCID 21913531, compound

HRID 1245889Notes

Reaction equation

HRID 1245889 reaction equation
C([O-])(=O)C.[NH4+:5].[CH2:6]([C:10]1[N:11]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[C:14](OC3C=CC=CC=3)[C:13]=2[N:27]=1)[CH2:7][CH2:8][CH3:9]>C(OCC)(=O)C>[CH2:6]([C:10]1[N:11]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:12]2[C:17]([CH3:18])=[C:16]([CH3:19])[N:15]=[C:14]([NH2:5])[C:13]=2[N:27]=1)[CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 21912905HCID 21912905, compound

Product 1

HCID 21913531HCID 21913531, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A sealed tube containing ammonium acetate (7.5 g) and 2-butyl-6,7-dimethyl-4-phenoxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridine (0.75 g) from Part C was heated in an oil bath to 150° C. for 48 hours. The reaction reached 70% completion and was allowed to cool to room temperature. The reaction mixture was then dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The product was passed through a silica gel column using 10/90 methanol/ethyl acetate as the eluant. To remove impurities, the product was recrystallized twice from acetonitrile with charcoal. The resulting white crystals were crushed and dried to yield 2-butyl-6,7-dimethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 130.0–132.0° C.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customTo remove impurities
  6. customthe product was recrystallized twice from acetonitrile with charcoal
  7. customThe resulting white crystals were crushed
  8. customdried

Sources & evidence

ORD record
ord-fc31e56618514a33b001c056f12ed350
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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