Sodium Iodide → HCID 86614003, compound

HRID 643002Notes

Reaction equation

HRID 643002 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[C:18]([CH2:20][C:21]4[CH:25]=[CH:24][S:23][C:22]=4[C:26]([NH2:28])=[O:27])[N:17]=[CH:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.[Na+].[I-].C[Si](Cl)(C)C>C(C#N)(C)=O>[O:2]=[C:3]1[C:8]([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH:19]=[C:18]([CH2:20][C:21]4[CH:25]=[CH:24][S:23][C:22]=4[C:26]([NH2:28])=[O:27])[N:17]=[CH:16]3)=[CH:13][CH:14]=2)=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86614001HCID 86614001, compound

Product 1

HCID 86614003HCID 86614003, compound

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-N-((1-(4-(2-methoxypyridin-3-yl)phenyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (0.01 g, 0.024 mmol) in AcCN (1 mL) was added NaI (0.011 g, 0.072 mmol) and TMSCl (0.045 mL, 0.36 mmol). After heating at 80° C. for 90 min, the reaction mixture was cooled to room temperature, and purified by preparative HPLC to yield 5-chloro-N-((1-(4-(2-oxo-1,2-dihydropyridin-3-yl)phenyl-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (MS 411.0, 413.0 (M+H) Cl pattern).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f9d71a228ae74c189ecb3151f0557460
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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