Water → HCID 66835926, compound

HRID 572856Notes

Reaction equation

HRID 572856 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH:17]([O:32][CH:33]1[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1)[C:18]1[CH:19]=[C:20]([S:24][CH2:25][CH2:26]OS(C)(=O)=O)[CH:21]=[CH:22][CH:23]=1.O>CN(C)C=O>[CH3:39][N:36]1[CH2:37][CH2:38][CH:33]([O:32][CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24][CH2:25][CH2:26][N:2]3[N:3]=[CH:4][CH:5]=[N:1]3)[CH:19]=2)[C:9]2[S:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 86695323HCID 86695323, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 66835926HCID 66835926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1,2,3-triazole (36.5 mg) in N,N-dimethylformamide (1 mL) is added a dispersion of sodium hydride 60% in mineral oil (1 molar equivalent). The reaction mixture is stirred at room temperature for 15 minutes, then a solution of methanesulfonic acid 2-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}ethyl ester (85 mg) in N,N-dimethylformamide (1 mL) is added. The reaction mixture is stirred at 60° C. overnight. Water is added and the aqueous phase is extracted by ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (gradient dichloromethane/methanol/ammonia 100/0/0 to 90/10/1) to afford 2-{(1-methylpiperidin-4-yloxy)[3-(2-[1,2,3]triazol-2-yl-ethylsulfanyl)phenyl]methyl}benzothiazole.

Workup

  1. stirringThe reaction mixture is stirred at 60° C. overnight
  2. extractionthe aqueous phase is extracted by ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography (gradient dichloromethane/methanol/ammonia 100/0/0 to 90/10/1)

Sources & evidence

ORD record
ord-ded319fa3c2e4942a15712ce27b427c5
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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