Chlorotrimethylsilane → HCID 10231820, compound

HRID 1835326Notes

Reaction equation

HRID 1835326 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:28])[C:9](=[O:27])[C:10]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH:3]=1.C[Si](C)(C)Cl.[C:41](Cl)(=[O:47])[CH2:42][CH2:43][C:44](Cl)=[O:45]>N1C=CC=CC=1>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:18]=[C:13]([C:10]([CH3:12])([CH3:11])[C:9]([N:8]([C:5]2[CH:6]=[N:7][C:2]([N:1]3[C:44](=[O:45])[CH2:43][CH2:42][C:41]3=[O:47])=[CH:3][C:4]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH3:28])=[O:27])[CH:14]=[C:15]([C:23]([F:26])([F:24])[F:25])[CH:16]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 10970Succinyl chlorideHCID 9913704HCID 9913704, compound

Product 1

HCID 10231820HCID 10231820, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 100 mg (0.20 mmol) N-(6-amino-4-o-tolyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide in 3 ml pyridine were added 54 mg (0.50 mmol) trimethylchlorosilane at room temperature. After stirring for 15 min, this mixture was added slowly under stirring to 155 mg (1.0 mmol) succinyl chloride and stirring was continued overnight. The solvent was removed in vacuo and the residue was purified by flash-chromatography to give 29 mg (25%) of the title compound as white solid.

Workup

  1. additionthis mixture was added slowly
  2. stirringstirring
  3. waitwas continued overnight
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-362875a451914bcf9dc54907b7358df6
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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