Hydrochloric Acid → HCID 178521635, compound

HRID 1846793Notes

Reaction equation

HRID 1846793 reaction equation
Cl.C(O)(C)C.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][C@H:16]1[CH2:19][C@@H:18]([O:20]CC2C=CC=CC=2)[CH2:17]1.C([O-])(O)=O.[Na+]>CCO.[Pd]>[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:15][C@@H:16]1[CH2:17][C@H:18]([OH:20])[CH2:19]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 178420425HCID 178420425, compound

Product 1

HCID 178521635HCID 178521635, compoundYield 113.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of hydrogen chloride (5-6 N) in isopropyl alcohol (5 mL, 25 mmol), cis-benzothiazol-2-yl-(3-benzyloxy-cyclobutyl)-amine (500 mg, 1.6 mmol), and palladium black (250 mg, 50% wt percent) in EtOH (20 mL) under hydrogen atmosphere (balloon) was heated to 70° C. for 20 h. Then it was cooled to RT and solid NaHCO3 (500 mg) was added. The mixture was stirred until gas evolution ceased. The palladium was filtered off using Celite® and the filtrate was concentrated in vacuo to give oil (400 mg), which was used for next step without further purification.

Workup

  1. temperatureThen it was cooled to RT
  2. filtrationThe palladium was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c7b5946345d84ec9854af93e5b99d281
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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