Triethylamine → HCID 117840045, compound

HRID 1477731Notes

Reaction equation

HRID 1477731 reaction equation
Cl[CH:2]1[CH2:7][N:6]([C:8]2[N:13]=[CH:12][N:11]([CH2:14][C:15]3[S:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[C:10](=[O:24])[N:9]=2)[CH2:5][CH:4]=[C:3]1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.C(N(CC)CC)C.[C-]#N.[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:3]2[CH:4]=[CH:5][N:6]([C:8]3[N:13]=[CH:12][N:11]([CH2:14][C:15]4[S:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=4)[C:10](=[O:24])[N:9]=3)[CH2:7][CH:2]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 117839648HCID 117839648, compound

Product 1

HCID 117840045HCID 117840045, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide solution (1.0 mL) of 4-[5-chloro-4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thio phen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (10.0 mg, 0.0212 mmol) synthesized in Reference Synthesis Example 353, triethylamine (10.0 μL, 0.0717 mmol) and potassium cyanide (10.0 mg, 0.154 mmol) were added and the resultant mixture was stirred at room temperature for 2.5 hours and at 80° C. for 40 minutes. After the completion of the reaction, to the reaction solution, saturated sodium bicarbonate aqueous solution 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 (hexane/ethyl acetate=1/1→0/1) to obtain the title compound (0.7 mg, yield: 8%).

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 (hexane/ethyl acetate=1/1→0/1)

Sources & evidence

ORD record
ord-d0337149449c420f90cc613cbca4b786
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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