Potassium bis(trimethylsilyl)amide → HCID 69652769, compound

HRID 1823287Notes

Reaction equation

HRID 1823287 reaction equation
[CH2:1]([O:8][C:9](=[O:35])[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][N:30]=[CH:29][C:28]=3[Cl:34])=[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:35])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:32]3[C:27](=[C:28]([Cl:34])[CH:29]=[N: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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69652677HCID 69652677, compound

Product 1

HCID 69652769HCID 69652769, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve (3-{[3-(3,5-dichloro-pyridin-4-yl)-5-methyl-isoxazole-4-carbonyl]amino}-cyclohexylmethyl)-carbamic acid benzyl ester (0.60 g, 0.0012 mol) 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, 2.32 mL, 0.0012 mol) and stir for 20 min. at ambient temperature. Quench the dark mixture with water and follow by the adding solid sodium chloride. Extract with ethyl acetate and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane to give 0.33 g (58%) of the desired product. MS(ES): (M+1)+ 481.0 m/z.

Workup

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

Sources & evidence

ORD record
ord-26776074b6374165bd0056103f31d406
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

Loading…