Triethylamine → HCID 86653002, compound

HRID 242080Notes

Reaction equation

HRID 242080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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][NH:13]3)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:32]([N:34](CC)CC)[CH3:33].BrCC#N>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([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[CH2:33][C:32]#[N:34])[CH2:9][CH2:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 58246215HCID 58246215, compound

Product 1

HCID 86653002HCID 86653002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[2-({1-[1-(3-Chlorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (70 mg, 0.14 mmol, cf. example 49) was dissolved in dry dichloromethane (0.5 mL). Triethylamine (35.5 mg, 0.35 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. After addition of 2-bromoacetonitrile (20 mg, 0.168 mmol) stirring at room temperature was continued over night. The reaction mixture was diluted with dichloromethane and washed with aqueous saturated NaHCO3 solution (5 mL) and water (5 mL). The organic phase was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:methanol=200:1). Yield: 35 mg (0.07 mmol, 50%).

Workup

  1. stirringstirring at room temperature
  2. waitwas continued over night
  3. washwashed with aqueous saturated NaHCO3 solution (5 mL) and water (5 mL)
  4. dry with materialThe organic phase was 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-7c25937baaa34390a025a4f957741f5d
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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