Dimethylamine → HCID 117839789, compound

HRID 1477718Notes

Reaction equation

HRID 1477718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:19]=[C:18]([CH2:20]O)[N:17]([CH2:22][C:23]4[S:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=4)[C:16](=[O:32])[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:33]([N:35](CC)[CH2:36]C)C.CS(Cl)(=O)=O.CNC>O1CCOCC1.ClCCl>[CH3:33][N:35]([CH2:20][C:18]1[N:17]([CH2:22][C:23]2[S:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=2)[C:16](=[O:32])[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:13][CH2:12]2)[N:19]=1)[CH3:36]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117839181HCID 117839181, compound

Product 1

HCID 117839789HCID 117839789, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a dichloromethane solution (1.5 mL) of 4-[4-(4-fluorophenyl)piperazin-1-yl]-6-(hydroxymethyl)-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (10.0 mg, 21.3 μmol) synthesized in Synthesis Example 458b, triethylamine (6.0 μL, 42.6 μmol) and methanesulfonyl chloride (2.4 μL, 32.0 μmol) were added and the resultant mixture was stirred at room temperature for 1 hour and 30 minutes. The volume of the reaction solution was divided in half. To one of the divided reaction solution, dimethylamine (20 μL) and 1,4-dioxane (4.0 mL) were added and the resultant mixture was stirred at 90° C. for 20 minutes. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (1.05 mg, yield: 20%).

Workup

  1. additionwere added
  2. additionwere added
  3. customAfter the completion of the reaction
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-49b5db969b6d4ebf81f2009950c57217
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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