Acetonitrile → HCID 117840122, compound

HRID 1477725Notes

Reaction equation

HRID 1477725 reaction equation
C(#N)C.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)[C:19](=[O:31])[N:18]=3)[CH2:13][CH:12]=2)=[CH:7][CH:6]=1.[OH-].[K+].C(OP([C:42](Br)([F:44])[F:43])(=O)OCC)C>C(OCC)C.O>[F:43][CH:42]([F:44])[O:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:20]2[CH:21]=[N:22][C:17]([N:14]3[CH2:15][CH2:16][C:11]([C:8]4[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=4)=[CH:12][CH2:13]3)=[N:18][C:19]2=[O:31])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 144101Bromodifluoromethyl diethylphosphonateHCID 117839212HCID 117839212, compound

Product 1

HCID 117840122HCID 117840122, compoundYield 12.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To an acetonitrile (1.0 mL)-water (1.0 mL) solution of 4-[4-(4-fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-1-(4-hydroxybenzyl)-1,3,5-triazin-2(1H)-one (15.0 mg, 0.0396 mmol) synthesized in Synthesis Example 483a, potassium hydroxide (44.5 mg, 0.793 mmol) was added and while stirring the resultant reaction solution at −78° C., to the reaction solution, diethyl(bromodifluoromethyl)phosphonate (14.1 μL, 0.0794 mmol) was added, followed by stirring the resultant reaction solution at room temperature for 2 and a half hours. After the completion of the reaction, extraction with diethyl ether from the reaction solution was performed. The organic layer was dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography to obtain the title compound (2.10 mg, yield: 11%).

Workup

  1. additionwas added
  2. customreaction solution at −78° C.
  3. stirringby stirring the resultant
  4. customreaction solution at room temperature for 2 and a half hours
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa658d830d7d43499e991aad5784f974
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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