Triethylamine → HCID 86653002, compound

HRID 1850860Notes

Reaction equation

HRID 1850860 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-290f6b7f1a5944ff99ce990b3fd4fa36
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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