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

HRID 336317Notes

Reaction equation

HRID 336317 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-89f0e4aff4c146cf8fe9f4ca7fa80d13
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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