1,2-Epoxy-3-fluoropropane → 2-Chloro-5-[1-(3-fluoro-2-hydroxy-propyl)-1H-imidazol-4-yl]-N-(1-hydroxy-cycloheptylmethyl)-benzamide

HRID 456888

Reaction equation

HRID 456888 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[CH:22][NH:23][CH:24]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[F:25][CH2:26][CH:27]1[CH2:29][O:28]1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[CH:22][N:23]([CH2:29][CH:27]([OH:28])[CH2:26][F:25])[CH:24]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5]

Participants

5

Reactant 2

HCID 104181,2-Epoxy-3-fluoropropaneHCID 178523109HCID 178523109, compound

Product 1

HCID 251928492-Chloro-5-[1-(3-fluoro-2-hydroxy-propyl)-1H-imidazol-4-yl]-N-(1-hydroxy-cycloheptylmethyl)-benzamideYield 87.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(1H-imidazol-4-yl)-benzamide(5 mg, 0.014 mmol) and 2-fluoromethyl-oxirane (0.06 mL, 0.086 mmol) in N,N-dimethylformamide (0.2 mL) was heated at 65° C. in a sealed tube for 20 h. The mixture was diluted with ethyl acetate and washed with water, and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (5.2 mg).

Workup

  1. washwashed with water, and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25b34376ab184fa0acc30d37729b6680
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Linked notes

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