Imidazole → HCID 58452309, compound

HRID 70500Notes

Reaction equation

HRID 70500 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Cl:14][C:15]1[CH:16]=[C:17]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([O:36][CH3:37])[N:30]=2)=[O:28])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26].[Cl-].[NH4+]>CN(C)C=O>[Si:5]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([C:27]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([O:36][CH3:37])[N:30]=2)=[O:28])=[CH:16][C:15]=1[Cl:14])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67398017[3-Chloro-4-(4-hydroxybutoxy)phenyl](5-chloro-6-methoxypyridin-2-yl)methanone

Product 1

HCID 58452309HCID 58452309, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylchlorosilane (240 mg) and imidazole (108 mg) were sequentially added to a solution of [3-chloro-4-(4-hydroxybutoxy)phenyl](5-chloro-6-methoxypyridin-2-yl)methanone (391 mg) in N,N-dimethylformamide (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 4.5 hours. The reaction solution was ice-cooled and a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→10:1) to give the title compound (389 mg, 76%).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→10:1)

Sources & evidence

ORD record
ord-80ef1efcfaeb49bab20986a2800b934c
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…