Trimethylsilyl iodide → HCID 45275136, compound

HRID 1622349Notes

Reaction equation

HRID 1622349 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[C:30]([Cl:31])=[CH:29][N:28]=[CH:27][C:26]=3[Cl:32])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C[Si](I)(C)C>C(Cl)Cl>[Cl:31][C:30]1[CH:29]=[N:28][CH:27]=[C:26]([Cl:32])[C:25]=1[N:22]1[CH2:21][CH2:20][CH:19]([C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[O:18])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 58378283HCID 58378283, compound

Product 1

HCID 45275136HCID 45275136, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl-4-(1-(3,5-dichloropyridin-4-yl)piperidine-4-carbonyl)piperazine-1-carboxylate 13 (40 mg, 0.080 mmol) in DCM (1 mL), cooled to 0° C. was added trimethylsilyliodide (24 μL, 0.16 mmol) and the solution was stirred at this temperature for 90 min, after which time trimethylsilyl iodide (48 μL, 0.32 mmol) was added and the mixture warmed to room temperature. After stirring for a further 45 min, the solution was concentrated under reduced pressure and the crude product was purified on an SCX-2 cartridge (MeOH followed by 0.5 M NH3 in MeOH) to furnish the title compound as a yellow solid (27 mg, 94%), m.p. 256-258° C.; m/z (ESI) C15H20C12N4NaO requires 365.0906, found [M+Na]+ 365.0909.

Workup

  1. stirringAfter stirring for a further 45 min
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe crude product was purified on an SCX-2 cartridge (MeOH followed by 0.5 M NH3 in MeOH)

Sources & evidence

ORD record
ord-bea454855ee049fd8c1fd1207a7697d6
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…