Dimethylamine → 1-{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-yl}-n,n-dimethylmethanamine

HRID 1950888Notes

Reaction equation

HRID 1950888 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26]O)[CH:14]=3)[O:10][N:9]=2)[CH:7]=1.[CH2:30]([N:32](C(C)C)[CH:33](C)C)C.CS(Cl)(=O)=O.CNC>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:15]([CH2:26][N:32]([CH3:33])[CH3:30])[CH:14]=3)[O:10][N:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 25255481{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-YL]-2'-methylbiphenyl-2-YL}methanol

Product 1

HCID 252554821-{4-[3-(5-Fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2'-methylbiphenyl-2-yl}-n,n-dimethylmethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 77 (115 mg; 0.29 mmol; 1 eq.) in DCM (6 mL) is added at 0° C. N-ethyldiisopropylamine (250 μL; 1.47 mmol; 5 eq.) and methanesulfonyl chloride (27 μL; 0.35 mmol; 1.2 eq.). After 15 min, dimethylamine (2M; 440 μL; 0.88 mmol; 3 eq.) was added and the reaction mixture stirred at room temperature for 2 hours. Water (5 mL) was added and the organic layer washed with water. The organic phase was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by mass triggered preparative HPLC (increasing amount of ACN in water) to afford the title compound as a brown oil.

Workup

  1. washthe organic layer washed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by mass
  5. temperatureHPLC (increasing amount of ACN in water)

Sources & evidence

ORD record
ord-465404e0de6a4837a234626af3c18f9f
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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