Potassium bis(trimethylsilyl)amide → HCID 69652652, compound

HRID 1823293Notes

Reaction equation

HRID 1823293 reaction equation
[CH2:1]([O:8][C:9](=[O:38])[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](Cl)=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[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:38])[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]=[C:30]([C:34]([F:37])([F:36])[F:35])[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 69652710HCID 69652710, compound

Product 1

HCID 69652652HCID 69652652, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve (3-{[3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (600 mg, 1.09 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, 2.62 mL, 1.31 mmol) and stir for 10 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 200 mg (36%) of the desired product as a light foam. MS(ES): (M+1)+ 515.2, 516.2 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-e0337ec8ef104eec9f6e047a4a44d5b7
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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