Dimethylformamide → HCID 117839717, compound

HRID 1477734Notes

Reaction equation

HRID 1477734 reaction equation
CN(C)C=O.CS(O[CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:18]=[C:19]([CH3:34])[N:20]([CH2:24][C:25]3[S:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=3)[C:21](=[O:23])[N:22]=2)[CH2:13][CH2:12]1)(=O)=O.[Br:35][C:36]1[CH:37]=[N:38][NH:39][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Br:35][C:36]1[CH:37]=[N:38][N:39]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[C:19]([CH3:34])[N:20]([CH2:24][C:25]4[S:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=4)[C:21](=[O:23])[N:22]=3)[CH2:13][CH2:12]2)[CH:40]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 117839810HCID 117839810, compound

Product 1

HCID 117839717HCID 117839717, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide solution (1.0 mL) of 1-(6-methyl-4-oxo-5-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-4,5-dihydro-1,3,5-triazin-2-yl)piperidin-4-yl methanesulfonate (45.2 mg, 0.100 mmol) synthesized in Reference Synthesis Example 349, 4-bromo-1H-pyrazole (29.4 mg, 0.200 mmol) and potassium carbonate (27.6 mg, 0.200 mmol) were added and the resultant mixture was stirred at 100° C. for 1 hour. After the completion of the reaction, to the reaction solution, water was added and extraction with ethyl acetate from the reaction solution was performed. The organic layer was dried over anhydrous sodium sulfate and was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (24.4 mg, yield: 48%).

Workup

  1. additionwere added
  2. customAfter the completion of the reaction
  3. extractionextraction with ethyl acetate from the reaction solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationwas concentrated under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e4786faa1ca847b9aa92e05c5f7b1eb7
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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