Water → HCID 59569012, compound

HRID 1517188Notes

Reaction equation

HRID 1517188 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH2:17][S:16][C:15](=[O:18])[NH:14][N:13]=3)=[CH:11][C:6]=2[N:5]=[C:4]1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[CH3:2].Br[CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH2:17][S:16][C:15](=[O:18])[N:14]([CH2:28][CH2:29][O:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[N:13]=3)=[CH:11][C:6]=2[N:5]=[C:4]1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 59569018HCID 59569018, compound

Product 1

HCID 59569012HCID 59569012, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 200 mg (0.55 mM) of 5-[1-ethyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in 4 ml of dimethylformamide are added 91 μl (0.6 mM) of 2-(2-bromoethoxy)tetrahydro-2H-pyran and 533.5 mg (1.64 mM) of caesium carbonate. The reaction medium is then stirred at room temperature for 16 hours. Demineralised water is added and the organic phase is isolated, washed with demineralised water and then dried over anhydrous sodium sulfate. The solvent is then evaporated off under vacuum and the residue is purified by chromatography on silica, using a dichloromethane/acetone mixture (90/10) as eluent, to give 200 mg of 5-[1-ethyl-2-(3-methoxyphenyl)-1H-benzimidazol-5-yl]-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-3,6-dihydro-2H-1,3,4-thiadiazin-2-one in the form of an oil.

Workup

  1. customthe organic phase is isolated
  2. washwashed with demineralised water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is then evaporated off under vacuum
  5. customthe residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-9096e9624cfa43cb89e96743902f2624
Source dataset
uspto-grants-2012_07
Patent number
US08232272B2

Reaction notes

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