Water → HCID 11671161, compound

HRID 916558Notes

Reaction equation

HRID 916558 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]([OH:37])[CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[N:26]=[C:25]([C:27]5[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=5)[O:24][N:23]=4)[CH2:17][CH2:16]3)=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH3:40]I.O>C1(C)C=CC=CC=1>[CH3:40][O:37][CH:13]([CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:21][C:22]2[N:26]=[C:25]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[O:24][N:23]=2)[CH2:19][CH2:20]1)[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9936917HCID 9936917, compound

Product 1

HCID 11671161HCID 11671161, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3-(2-methylbenzothiazol-5-yloxy)-1-[4-({5-[4-(trifluoromethyl)phenyl]-(1,2,4-oxadiazol-3-yl)}methyl)piperazinyl]propan-2-ol (0.10 g) in toluene (6 ml) was added to a suspension of sodium hydride (0.09 g) in toluene (2 ml) at 0° C. The mixture was stirred at 100° C. for 2 hours, then cooled to 0° C. Methyl iodide (0.14 ml) was then added, and the mixture stirred overnight at room temperature. After slow addition of water the mixture was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and the solvent removed under reduced pressure. The residue was purified by flash chromatography (3% methanol in methylene chloride), to provide 5-{2-methoxy-3-[4-({5-[4-(trifluoromethyl)phenyl](1,2,4-oxadiazol-3-yl)}methyl)piperazinyl]propoxy}-2-methylbenzothiazole (0.0075 g).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture stirred overnight at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (3% methanol in methylene chloride)

Sources & evidence

ORD record
ord-a777957075504cc9a261b6ecc529aca3
Source dataset
uspto-grants-2007_09
Patent number
US07271169B2

Reaction notes

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