HCID 58248786, compound → HCID 51347267, compound

HRID 2040404Notes

Reaction equation

HRID 2040404 reaction equation
[CH2:1]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@H:18]3[CH2:20][O:19]3)=[CH:12][CH:11]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]>C(NCC)C.C1COCC1>[CH2:1]([C:5]1[N:6]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[CH:23][CH:22]=2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C@H:18]([OH:19])[CH2:20][N:6]([CH2:7][CH3:8])[CH2:5][CH3:1])=[CH:12][CH:11]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 58248786HCID 58248786, compound2×

Product 1

HCID 51347267HCID 51347267, compound

Reagents, catalysts & solvents 2

HCID 8021DiethylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-4-[4-((R)-1-oxiranylmethoxy)-phenyl]-1H-imidazole (100 mg, 2.1 mmol, from intermediate A2) in 1 mL of diethylamine and 2 mL of THF was stirred at 76° C. for 1 h in a microwave reactor. Upon completion (determined by LC/MS), the reaction was evaporated in vacuo and purified by silica gel flash column chromatography using a gradient of EtOAc to 96% EtOAc/(2M NH3/MeOH) as an eluent to afford (R)-1-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-3-diethylamino-propan-2-ol.

Workup

  1. customUpon completion (determined by LC/MS), the reaction was evaporated in vacuo
  2. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-a6a831da18394bb99baddce56c55306d
Source dataset
uspto-grants-2013_11
Patent number
US08580833B2

Reaction notes

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