Potassium bis(trimethylsilyl)amide → HCID 136036463, compound

HRID 990241Notes

Reaction equation

HRID 990241 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:23])[C:13]3[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=3[N:15]=2)=[CH:8][C:7]([S:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[CH:6][N:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>N1C=CC=CC=1CO>[CH2:33]([N:30]1[CH2:31][CH2:32][N:27]([S:24]([C:7]2[CH:8]=[C:9]([C:10]3[NH:11][C:12](=[O:23])[C:13]4[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=4[N:15]=3)[C:4]([O:3][CH2:1][C:2]3[CH:7]=[CH:8][CH:9]=[CH:4][N:5]=3)=[N:5][CH:6]=2)(=[O:26])=[O:25])[CH2:28][CH2:29]1)[CH3:34]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 135977905HCID 135977905, compound

Product 1

HCID 136036463HCID 136036463, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 11474PiconolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the title compound of Example 124 (100 mg, 0.20 mmol) and potassium bis(trimethylsilyl)amide (204 mg, 1.02 mmol) in pyridine-2-methanol (2 ml) was stirred at 110° C. for 18 hours, then cooled. The solvent was removed by Kugelrohr distillation, and the residue was purified by column chromatography on silica gel, using dichloromethane: methanol (95:5) as eluant. This product was triturated with ether to afford the title compound (8 mg, 7%) as a solid.

Workup

  1. temperaturecooled
  2. customThe solvent was removed by Kugelrohr distillation
  3. customthe residue was purified by column chromatography on silica gel
  4. customThis product was triturated with ether

Sources & evidence

ORD record
ord-d77ec91867ab411ead9601eccfd40545
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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