Chlorotrimethylsilane → HCID 57897949, compound

HRID 1693528Notes

Reaction equation

HRID 1693528 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]=[CH:13][N:14]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:15]=2[NH:16][C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.C[Si](Cl)(C)C>>[CH2:27]([N:14]1[CH:13]=[N:12][C:11]2[C:9](=[O:10])[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[N:16][C:15]1=2)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 57897838HCID 57897838, compound

Product 1

HCID 57897949HCID 57897949, compoundYield 71%

Conditions

Temperature
100 °C

Procedure

The reaction mixture of 1-benzyl-5-(2,4-dichloro-benzoylamino)-1H-imidazole-4-carboxylic acid (4-chloro-phenyl)-amide (60 mg, 0.12 mmol), triethylamine (670 μL, 4.8 mmol) and trimethylsilyl chloride (303 μL, 2.4 mmol) is heated at 100° C. for 2 days. After cooled to room temperature, the resulting mixture is quenched with 1 N HQ and dichloromethane. The aqueous phase is extracted with dichloromethane. The organic phases is combined, ished with brine and dried over magnesium sulfate. Concentration followed by purification with chromatography gives the desired product (41 mg, 71% yield).

Workup

  1. temperatureAfter cooled to room temperature
  2. customthe resulting mixture is quenched with 1 N HQ and dichloromethane
  3. extractionThe aqueous phase is extracted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration
  6. customfollowed by purification with chromatography

Sources & evidence

ORD record
ord-9dd6fa5bf36e4726b772f7a6da3d42f0
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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