Phenol → HCID 21912905, compound

HRID 1352538Notes

Reaction equation

[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].[CH2:12]([C:16]1[N:17]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:18]2[C:23]([CH3:24])=[C:22]([CH3:25])[N:21]=[C:20](Cl)[C:19]=2[N:27]=1)[CH2:13][CH2:14][CH3:15]>COCCOCCOC>[CH2:12]([C:16]1[N:17]([CH2:28][CH2:29][O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:18]2[C:23]([CH3:24])=[C:22]([CH3:25])[N:21]=[C:20]([O:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:19]=2[N:27]=1)[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methoxyethyl ether (diglyme) (1.50 ml) and sodium hydride (60% in oil) (0.12 g) were combined and cooled to 0° C. Phenol (0.27 g) was added slowly in portions over 1 hour to allow for controlled release of hydrogen gas. 2-Butyl-4-chloro-6,7-dimethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]pyridine (0.96 g) from Part B was then added and the reaction mixture became dark brown. The reaction mixture was heated to reflux for 5 days, at which time HPLC analysis indicated the reaction was complete. The reaction mixture was cooled and washed with water. The mixture was filtered and the resulting solid was dried under vacuum at 60° C. overnight. NMR analysis of the product indicated sufficient purity for use of the product in the next step.

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for 5 days, at which time HPLC analysis
temperatureThe reaction mixture was cooled
washwashed with water
filtrationThe mixture was filtered
customthe resulting solid was dried under vacuum at 60° C. overnight

Sources & evidence

ORD record: ord-0fd5721727c24dc8a8ffc4f23e8de457
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220758B2

Reaction notes

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