Sodium Hydroxide → HCID 66835984, compound

HRID 2404449Notes

Reaction equation

HRID 2404449 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[N:26](COCC[Si](C)(C)C)[N:27]=[CH:28][CH:29]=3)[CH:20]=2)[C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH2:3]1.[OH-].[Na+]>Cl.O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[NH:26][N:27]=[CH:28][CH:29]=3)[CH:20]=2)[C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66836074HCID 66836074, compound

Product 1

HCID 66835984HCID 66835984, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2-((1-Methyl-piperidin-4-yloxy)-{3-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]-phenyl}-methyl)-benzothiazole (500 mg) in 5N hydrochloric acid (4 mL) is stirred overnight at room temperature. 30% sodium hydroxide solution is added to reach pH 10, and the reaction is diluted with water. The aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol from 100/0 to 90/10) to afford 2-{(1-methylpiperidin-4-yloxy)[3-(2H-pyrazol-3-yl)phenyl]methyl}benzothiazole melting at 90° C.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography (gradient dichloromethane/methanol from 100/0 to 90/10)

Sources & evidence

ORD record
ord-d2573ba1b3b64af08c90f9aaa8c27469
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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