N-methyl-2-pyrrolidone → HCID 117974290, compound

HRID 2272893Notes

Reaction equation

HRID 2272893 reaction equation
[H-].[Na+].CN1CCCC1=O.[CH2:10]([S:12][C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)[CH3:11].Cl[C:19]1[N:31]([CH3:32])[C:22]2=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=[C:21]2[N:20]=1>O>[CH2:10]([S:12][C:13]1[N:17]([C:19]2[N:31]([CH3:32])[C:22]3=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=[C:21]3[N:20]=2)[CH:16]=[CH:15][N:14]=1)[CH3:11]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 189575752-(Ethylsulfanyl)-1H-imidazoleHCID 117974229HCID 117974229, compound

Product 1

HCID 117974290HCID 117974290, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41 mg of sodium hydride (60% oil-based) was suspended into 4 ml of 1-methyl-2-pyrrolidone (NMP), and 0.13 g of 2-ethylthioimidazol was added under ice cooling. After stirring the mixture for 10 minutes, 0.2 g of 2-chloro-3-methyl-6-trifluoromethyl-3H-imidazo[4,5,b]pyridine was added, and the mixture was stirred under room temperature for 3 hours. Water was poured, and the deposited precipitate was obtained by filtration and was applied to a silica gel column chromatography to obtain 0.28 g of 2-(2-ethylthio-3H-imidazol-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5,b]pyridine (Compound of Present Invention (1)).

Workup

  1. additionwas added under ice cooling
  2. stirringthe mixture was stirred under room temperature for 3 hours
  3. customthe deposited precipitate was obtained by filtration

Sources & evidence

ORD record
ord-a24273b2a6ba4aa59e995a3e09ab65b1
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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