Hydrochloric Acid → HCID 66869221, compound

HRID 242072Notes

Reaction equation

HRID 242072 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]3[C:32](=O)[C:33]([F:36])([F:35])[F:34])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.B.[ClH:39]>O1CCCC1>[ClH:39].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]3[CH2:32][C:33]([F:35])([F:34])[F:36])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 86653001HCID 86653001, compound

Product 1

HCID 66869221HCID 66869221, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (49 mg, 0.09 mmol) was dissolved in dry tetrahydrofuran (0.6 mL) under an atmosphere of nitrogen. The solution was cooled to 0° C. and a 1M solution of borane in tetrahydrofuran (0.181 mL, 0.181 mmol) was added dropwise. The reaction mixture was warmed to room temperature and then heated under reflux for 2 h. The solvent was evaporated in vacuo, the residue was dissolved in dichloromethane (20 mL) and washed with water (10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The product was dissolved in dichloromethane (2 mL) and treated with 5N isopropanolic hydrochloric acid (27 μL, 0.135 mmol). The solvents were evaporated and the product was dried in vacuo. Yield: 45 mg (0.08 mmol, 88%).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperatureheated
  3. temperatureunder reflux for 2 h
  4. customThe solvent was evaporated in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  6. washwashed with water (10 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. dissolutionThe product was dissolved in dichloromethane (2 mL)
  10. customThe solvents were evaporated
  11. customthe product was dried in vacuo

Sources & evidence

ORD record
ord-a91f1fcd6793468daac1d92ac20c424e
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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