Trimethylsilyl iodide → HCID 68741132, compound

HRID 869922Notes

Reaction equation

HRID 869922 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:19]3([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:21][CH2:20]3)=[O:18])[N:10]=2)[CH:6]=[CH:5][N:4]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2([C:17]([NH:16][C:11]3[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([C:7]4[CH:6]=[CH:5][NH:4][C:3](=[O:2])[CH:8]=4)[N:10]=3)=[O:18])[CH2:21][CH2:20]2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68721785HCID 68721785, compound

Product 1

HCID 68741132HCID 68741132, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-(2′-Methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(4-methoxyphenyl)cyclopropanecarboxamide (TFA salt) (˜39 mg, ˜0.10 mmol) was dissolved in chloroform (1 mL) in a reaction tube. Trimethylsilyliodide (56 μL, 0.40 mmol was added and the reaction mixture was stirred at room temperature for 4 hours. The resulting material was filtered and evaporated under reduced pressure. The crude product was dissolved in DMSO (1 mL), filtered, and purified by reverse phase preparative HPLC to yield 1-(4-methoxyphenyl)-N-(5-methyl-6-(2-oxo-1,2-dihydropyridin-4-yl)pyridin-2-yl)cyclo-propanecarboxamide. ESI-MS m/z calc. 375.2. found 376.5 (M+1)+. Retention time 1.45 minutes.

Workup

  1. filtrationThe resulting material was filtered
  2. customevaporated under reduced pressure
  3. dissolutionThe crude product was dissolved in DMSO (1 mL)
  4. filtrationfiltered
  5. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-4415f3f6a0a44c72ab27ee4af6ad67e6
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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