(Diethylamino)sulfur trifluoride → HCID 117840873, compound

HRID 1477710Notes

Reaction equation

HRID 1477710 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH:17](O)[C:16]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[CH:15][CH2:14]3)=[N:9][C:8]2=[O:27])=[CH:4][CH:3]=1.C(N(S(F)(F)[F:36])CC)C>ClCCl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH:17]([F:36])[C:16]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[CH:15][CH2:14]3)=[N:9][C:8]2=[O:27])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 117839711HCID 117839711, compound

Product 1

HCID 117840873HCID 117840873, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane solution (1.0 mL) of 1-(4-chlorobenzyl)-4-[4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2(1H)-one (15 mg, 0.04 mmol) synthesized in Synthesis Example 90, (diethylamino)sulfur trifluoride (10 μL, 0.04 mmol) was added at 0° C. and the resultant mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, dichloromethane was added to the reaction solution and the resultant reaction solution was washed with saturated sodium bicarbonate water and brine. The resultant organic layer was dried over anhydrous sodium sulfate and was concentrated under reduced pressure. To the resultant residue, silica gel was added and the mixture was filtered, followed by washing the mixture with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain the title compound (7 mg, yield: 46%).

Workup

  1. additionwas added at 0° C.
  2. additionwas added to the reaction solution
  3. customthe resultant reaction solution
  4. washwas washed with saturated sodium bicarbonate water and brine
  5. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. additionTo the resultant residue, silica gel was added
  8. filtrationthe mixture was filtered
  9. washby washing the mixture with ethyl acetate
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ff9c4ce504f44e9b2eb956a989e0ebc
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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