Potassium bis(trimethylsilyl)amide → HCID 69652685, compound

HRID 1823281Notes

Reaction equation

HRID 1823281 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[CH:28]=[N:29][CH:30]=[CH:31][C:32]=3Cl)=[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](=[CH:28][N: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 69652730HCID 69652730, compound

Product 1

HCID 69652685HCID 69652685, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve (3-{[3-(4-chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (0.63 g, 0.0013 mol) in N,N-dimethylformamide (10 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 3.12 mL, 0.0016 mol) and stir for 15 min. at ambient temperature. Quench the dark mixture with water and follow by the addition of solid sodium chloride. Extract with ethyl acetate and wash the combined extracts with water and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane to give 0.47 g (81%) of the desired product as a white solid. MS(ES): (M+1)+ 447.2, 448.2 m/z.

Workup

  1. customQuench the dark mixture with water
  2. additionfollow by the addition of solid sodium chloride
  3. extractionExtract with ethyl acetate
  4. washwash the combined extracts with water
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate
  7. washelute over silica gel with methanol/dichloromethane

Sources & evidence

ORD record
ord-20bcfa2ad9b84ba09d0e2095332081d4
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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