Dimethylformamide → HCID 14127915, compound

HRID 520761Notes

Reaction equation

HRID 520761 reaction equation
CN(C)C=O.[F:6][C:7]([F:17])([F:16])[C:8]([N:10]=[C:11]1[NH:15][CH2:14][CH2:13][S:12]1)=[O:9].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:18][C:19]1[N:20]=[CH:21][C:22]([CH2:25][N:15]2[CH2:14][CH2:13][S:12][C:11]2=[N:10][C:8](=[O:9])[C:7]([F:6])([F:16])[F:17])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 178522584HCID 178522584, compound

Product 1

HCID 14127915HCID 14127915, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylformamide (2 mL) and tetrahydrofuran (18 mL) were added to 162 mg (0.82 mmol) of 2,2,2-trifluoro-N-(thiazolidin-2-ylidene)acetamide obtained by the above-described method, following which 198 mg of 2-chloro-5-chloromethylpyridine and 150 mg (1.09 mmol) of potassium carbonate were added, and the mixture was refluxed under heating for 20 hours. Following reaction completion, the reaction mixture was returned to room temperature, insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was purified on a TLC plate (two 0.5 mm plates, developed with 100% ethyl acetate), giving 230 mg of the target compound (yield, 87%).

Workup

  1. customobtained by the above-described method
  2. additionwere added
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 20 hours
  5. customreaction completion
  6. customwas returned to room temperature
  7. filtrationinsoluble matter was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe concentrate was purified on a TLC plate (two 0.5 mm plates, developed with 100% ethyl acetate)

Sources & evidence

ORD record
ord-fc77e0e62ce4444bb2129e6060513c4d
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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