Potassium bis(trimethylsilyl)amide → HCID 69652693, compound

HRID 1823292Notes

Reaction equation

HRID 1823292 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]2[C:22]([C:27]3[C:32](F)=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:23][O:24][C:25]=2[CH3:26])=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:32]3[C:27](=[N:28][CH:29]=[CH:30][CH:31]=3)[C:22]3=[N:23][O:24][C:25]([CH3:26])=[C:21]3[C:19]2=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69652747HCID 69652747, compound

Product 1

HCID 69652693HCID 69652693, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve (3-{[3-(3-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (260 mg, 0.56 mmol) in N,N-dimethylformamide (5 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 1.34 mL, 0.67 mmol) and stir for 15 min. at ambient temperature. Quench the dark mixture with water and follow by the adding solid sodium chloride. Extract with ethyl acetate and wash with water and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane to give 131 mg (53%) of the desired product. MS(ES): (M+1)+ 447.2, 448.2 m/z.

Workup

  1. customQuench the dark mixture with water
  2. extractionExtract with ethyl acetate
  3. washwash with water
  4. dry with materialdry over sodium sulfate
  5. concentrationConcentrate
  6. washelute over silica gel with methanol/dichloromethane

Sources & evidence

ORD record
ord-c39cd0659cd54673b8086efcfcef98d3
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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