2-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrile → 2-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amine

HRID 2167444Notes

Reaction equation

HRID 2167444 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]#[N:22])=[CH:15][CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])[N:4]=[CH:3]1>C1COCC1.C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([S:7]([N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][C:14]([CH:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:21][NH2:22])=[CH:15][CH:16]=3)[CH2:11]2)(=[O:8])=[O:9])[N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 667476862-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrile

Product 1

HCID 566426142-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropan-1-amineYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The synthesis was performed starting from 0.123 mmol of 2-(2-(1-methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrile, which was dissolved in THF (1 ml), after which 0.37 mmol of BH3 THF complex (1 M in THF) was added at 0° C. The mixture was warmed to room temperature and stirred for 2 h. The mixture was diluted with CH2Cl2 and washed with 1 N HCl, saturated NaHCO3 and H2O. The aqueous phase was extracted with CH2Cl2. Combined organic phase was dried over MgSO4 and filtered. Evaporation of the solvent gave 50 mg of the crude material. The material was purified by flash chromatography to yield 11 mg of a white solid (22%).

Workup

  1. washwashed with 1 N HCl, saturated NaHCO3 and H2O
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. dry with materialCombined organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. customgave 50 mg of the crude material
  7. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-c464a5f35367448292ab6b44dc136bbf
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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