Sodium hydride → HCID 57379002, compound

HRID 1184386Notes

Reaction equation

HRID 1184386 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:25][CH2:26][CH:27]3[CH2:29][CH2:28]3)=[N:10][CH:11]=[C:12]([CH:24]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18]/[C:17]/2=[N:22]\[OH:23])=[O:14])=[CH:4][CH:3]=1.[H-].[Na+].[F:32][C:33]([F:44])([F:43])[CH2:34]OS(C(F)(F)F)(=O)=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29]3)=[N:10][CH:11]=[C:12]([CH:24]=2)[C:13]([NH:15][C@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18]/[C:17]/2=[N:22]\[O:23][CH2:34][C:33]([F:44])([F:43])[F:32])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 88536600HCID 88536600, compound

Product 1

HCID 57379002HCID 57379002, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.100 g 5-(4-chloro-phenyl)-6-cyclopropylmethoxy-N-{(S)-2-[(E)-hydroxyimino]-cyclohexyl}-nicotinamide in 1.0 ml dimethylformamide was added 0.012 g sodium hydride 55% in oil and the mixture was stirred at room temperature for 30 min. To the resulting solution was added 0.037 ml (0.062 g, 1.1 equivalents) 2,2,2-trifluoroethyl-trifluoro-methanesulfonate and the mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate=95:5 to 50:50 to yield 0.040 g of the title compound as light yellow oil. MS (EI): 496.3 (M+H).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-ff5542ac5aaf4ad6aa7ad73542825285
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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