Hydrochloric Acid → N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-2-(1H-imidazol-2-yl)-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

HRID 1850862Notes

Reaction equation

HRID 1850862 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])=[CH:13][CH:14]=2)[CH:9]1[C:28]1([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:31][CH2:30][CH2:29]1)=[NH:7].Cl>C(#N)C>[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:28]2([CH:9]3[C:10]4[C:15](=[CH:14][CH:13]=[C:12]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])[CH:11]=4)[CH2:16][CH2:17][N:8]3[C:6]3[NH:5][CH:4]=[CH:3][N:7]=3)[CH2:29][CH2:30][CH2:31]2)=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178461078HCID 178461078, compound

Product 1

HCID 66868471N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-2-(1H-imidazol-2-yl)-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude N-(2,2-dimethoxyethyl)-1-[1-(4-fluorophenyl)cyclobutyl]-7-{2-[(propylsulfonyl)amino]ethoxy}-3,4-dihydroisoquinoline-2(1H)-carboximidamide (see above) was dissolved in acetonitrile (5 mL). Concentrated aqueous hydrochloric acid was added until the reaction mixture remained at pH 1. After stirring at room temperature over night the solvent was evaporated in vacuo. Water (10 mL) was added and the mixture was neutralized with aqueous saturated NaHCO3 solution. The mixture was extracted with dichloromethane (2×10 mL). The combined organic layers were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:methanol=80:1). Yield: 2.8 mg (5.5 μmol, 2%).

Workup

  1. customwas evaporated in vacuo
  2. additionWater (10 mL) was added
  3. extractionThe mixture was extracted with dichloromethane (2×10 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by flash chromatography (silica, dichloromethane

Sources & evidence

ORD record
ord-a2df894672094b1e95a7135795ba0038
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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