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

HRID 1988386Notes

Reaction equation

HRID 1988386 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-dd7b765acf4d4eb0b6e0d984452e1b8c
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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