Ammonium Acetate → HCID 9925765, compound

HRID 1007991Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]1[N:12]=[C:11](OC2C=CC=CC=2)[C:10]2[N:20]=[CH:21][N:22]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:9]=2[C:8]=1[CH3:32]>ClCCl>[CH3:6][C:7]1[N:12]=[C:11]([NH2:5])[C:10]2[N:20]=[CH:21][N:22]([CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:9]=2[C:8]=1[CH3:32]

Participants

Conditions

Temperature: 150 °C

Procedure

A sealed tube containing ammonium acetate (12.7 g) and 6,7-dimethyl-4-phenoxy-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridine (1.27 g) from Part E was heated to 150° C. for 36 hours. HPLC and TLC analysis indicated that the reaction was complete. The reaction was allowed to cool to room temperature. The resulting reaction mixture was then dissolved in dichloromethane (DCM) and washed with 20% aqueous sodium hydroxide. The basic layer was washed with DCM and the combined organic layers were dried with magnesium sulfate and concentrated under reduced pressure. The resulting oil was passed through a silica gel column using 95/5 dichloromethane/methanol as the eluant. The product was recrystallized from isopropyl alcohol, and the resulting white solid was dried under vacuum to provide 6,7-dimethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridin-4-amine, m.p. 197.0-199.0° C.

Workup

temperatureto cool to room temperature
customThe resulting reaction mixture
washwashed with 20% aqueous sodium hydroxide
washThe basic layer was washed with DCM
dry with materialthe combined organic layers were dried with magnesium sulfate
concentrationconcentrated under reduced pressure
customThe product was recrystallized from isopropyl alcohol
customthe resulting white solid was dried under vacuum

Sources & evidence

ORD record: ord-3e8dc1bb84804f41a3c1f3a1efda9c6d
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797718B2

Reaction notes

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