Hydrochloric Acid → HCID 66797199, compound

HRID 1487787Notes

Reaction equation

HRID 1487787 reaction equation
[ClH:1].Cl.C([O:10][C:11]1[CH:35]=[CH:34][C:14]2[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][N:21](C=O)[CH2:20][CH:19]3[CH2:26][O:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[S:17][C:13]=2[CH:12]=1)C1C=CC=CC=1.Cl.O>CCO>[ClH:1].[ClH:1].[ClH:1].[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([O:27][CH2:26][CH:19]2[CH2:20][NH:21][CH2:22][CH2:23][N:18]2[C:16]2[S:17][C:13]3[CH:12]=[C:11]([OH:10])[CH:35]=[CH:34][C:14]=3[N:15]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 866187484-(6-(Benzyloxy)benzo[d]thiazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carbaldehyde dihydrochloride

Product 1

HCID 66797199HCID 66797199, compoundYield 200.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(6-(Benzyloxy)benzo[d]thiazol-2-yl)-3-((pyridin-3-yloxy)methyl)piperazine-1-carbaldehyde dihydrochloride (130 mg, 0.244 mmol) and HCl (conc., 1.0 mL) were heated to 100° C. in EtOH (1 mL) and water (1 mL) for 2 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure and purified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient). The desired fractions were concentrated under reduced pressure, dissolved in MeOH (1 mL) and treated with 4 M HCl in 1,4-dioxane (6 mL). This was concentrated under reduced pressure, yielding 73.8 mg (67%) of the title compound as a white solid. LC-MS: RT=3.45 min, [M+H]+; =343.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by HPLC (5 to 50% MeCN/0.1% TFA in H2O/0.1% TFA gradient)
  3. concentrationThe desired fractions were concentrated under reduced pressure
  4. dissolutiondissolved in MeOH (1 mL)
  5. additiontreated with 4 M HCl in 1,4-dioxane (6 mL)
  6. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4cc974227f840bb9750ff400d938eb3
Source dataset
uspto-grants-2016_08
Patent number
US09428522B2

Reaction notes

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