Sodium dicyanamide → HCID 178461077, compound

HRID 1850831Notes

Reaction equation

HRID 1850831 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:21]=4)[CH2:16][CH2:15][NH:14]3)[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[N-:33]([C:36]#[N:37])[C:34]#[N:35].[Na+]>C(O)CCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[CH:21]=4)[CH2:16][CH2:15][N:14]3[C:36](=[NH:37])[NH:33][C:34]#[N:35])[CH2:10][CH2:11][CH2:12]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 444652761-(1-(4-Chlorophenyl)cyclobutyl)-7-(2-(propylsulfonamido)ethoxy)-1,2,3,4-tetrahydroisoquinolinium chloride

Product 1

HCID 178461077HCID 178461077, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Propane-1-sulfonic acid (2-{1-[1-(4-chloro-phenyl)-cyclobutyl]-1,2,3,4-tetrahydro-isoquinolin-7-yloxy}-ethyl)-amide hydrochloride (example 4, 95.0 mg, 0.19 mmol) was dissolved in 1-butanol (10 ml) and sodium dicyanamide (42.3 mg, 0.48 mmol) was added. The reaction mixture was stirred under reflux. After 4 h, the solvent was removed and dichloromethane was added. The resulting precipitate was removed by filtration and purified by flash column chromatography on silica with dichloromethane/methanol 10:0→94:6. The product was obtained as a solid (30.0 mg, 0.06 mmol, 30.0%).

Workup

  1. temperatureunder reflux
  2. customthe solvent was removed
  3. additiondichloromethane was added
  4. customThe resulting precipitate was removed by filtration
  5. custompurified by flash column chromatography on silica with dichloromethane/methanol 10:0→94:6

Sources & evidence

ORD record
ord-01b4eed141f7462dbf4bce1bf48485d3
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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