HCID 178474136, compound → HCID 178474135, compound

HRID 1990903Notes

Reaction equation

HRID 1990903 reaction equation
[OH:1][CH2:2][C:3]1[NH:7][C:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)=[N:5][C:4]=1[CH3:18]>C1COCC1.O=[Mn]=O>[CH:2]([C:3]1[NH:7][C:6]([C:8]2[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=2)=[N:5][C:4]=1[CH3:18])=[O:1]

Participants

4

Reactant 1

HCID 178474136HCID 178474136, compound

Product 1

HCID 178474135HCID 178474135, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(5-hydroxymethyl-4-methyl-1H-imidazol-2-yl)-phenyl]-acetamide (0.064 g, 0.23 mmol, 1.0 equiv) in THF (2 mL) was added activated MnO2 (0.20 g, 2.3 mmol, 10.0 equiv). The reaction mixture was stirred vigorously for 18 h at ambient temperature and then filtered through Hyflo Super Cel. The organic phase was concentrated by evaporation under reduced pressure and the crude reaction product directly used in the following reductive alkylation step without further purification assuming quantitative conversion. MS (ESI): 244.3 [M+H]+.

Workup

  1. filtrationfiltered through Hyflo Super Cel
  2. concentrationThe organic phase was concentrated by evaporation under reduced pressure
  3. customthe crude reaction product
  4. customdirectly used in the following reductive alkylation step without further purification

Sources & evidence

ORD record
ord-c8ecbef8581c481cb6648e8ca54457e7
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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