Hydrochloric Acid → HCID 58246282, compound

HRID 1850883Notes

Reaction equation

HRID 1850883 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][N:17]=[C:18]2[C:21]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[N:26]=3)[CH2:24][CH2:23][CH2:22]2)=[CH:13][CH:12]=1)(C)(C)C.Cl>>[Cl:31][C:27]1[N:26]=[C:25]([C:21]2([C:18]3[C:19]4[C:14](=[CH:13][CH:12]=[C:11]([O:10][CH2:9][CH2:8][NH2:7])[CH:20]=4)[CH2:15][CH2:16][N:17]=3)[CH2:24][CH2:23][CH2:22]2)[CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86653005HCID 86653005, compound

Product 1

HCID 58246282HCID 58246282, compound

Procedure

tert-Butyl[2-({1-[1-(6-chloropyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]carbamate (300 mg, 0.658 mmol) were dissolved in isopropanole (4 ml). 5N isopropanolic hydrochloric acid (2 ml) was added and the reaction mixture stirred at room temperature for 4 hours. The solvent was evaporated in vacuo and dichloromethane (20 mL) was added. 1N aqueous sodium hydroxide solution was added dropwise until pH 10 was reached. The phases were separated and the aqueous layer was extracted twice with dichloromethane. The combined organich layers were dried (MgSO4) and concentrated in vacuo. The crude product was used for the next step without further purification. Yield: 150 mg (0.422 mmol, 64%).

Workup

  1. customThe solvent was evaporated in vacuo and dichloromethane (20 mL)
  2. additionwas added
  3. addition1N aqueous sodium hydroxide solution was added dropwise until pH 10
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe combined organich layers were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-a35285f8ee624c5fb9ab6c0fe09c3b52
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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