1-methyl-1H-imidazole-4-sulfonyl chloride → 2-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrile

HRID 2167443Notes

Reaction equation

HRID 2167443 reaction equation
[C:1]1([CH2:7][CH:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][NH:17][CH2:18]3)=[CH:13][CH:12]=2)[C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][N:22]1[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[N:24]=[CH:23]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:21][N:22]1[CH:26]=[C:25]([S:27]([N:17]2[CH2:16][CH2:15][C:14]3[C:19](=[CH:20][C:11]([CH:8]([CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:9]#[N:10])=[CH:12][CH:13]=3)[CH2:18]2)(=[O:29])=[O:28])[N:24]=[CH:23]1

Participants

5

Reactant 2

HCID 27368871-methyl-1H-imidazole-4-sulfonyl chloride2×HCID 667475123-Phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-yl)propanenitrile

Product 1

HCID 667476862-(2-(1-Methyl-1H-imidazol-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-phenylpropanenitrileYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.135 mmol 3-phenyl-2-(1,2,3,4-tetrahydroisoquinolin-7-yl)propanenitrile in 2 ml CH2Cl2 were added 0.203 mmol DMAP and 0.162 mmol 1-methyl-1H-imidazole-4-sulfonyl chloride. The mixture was stirred at room temperature for 3 h. Additional 0.162 mmol 1-methyl-1H-imidazole-4-sulfonyl chloride were added and the mixture was stirred for 3 d. The mixture was diluted with CH2Cl2 and washed with 1N HCl, saturated NaHCO3 and H2O. The combined aqueous layers were extracted with CH2Cl2. The combined organic phase was dried over MgSO4 and filtered. Evaporation of the solvent gave 90 mg of the crude material. The material was purified by flash chromatography to yield 53 mg of a white solid (97%).

Workup

  1. stirringthe mixture was stirred for 3 d
  2. washwashed with 1N HCl, saturated NaHCO3 and H2O
  3. extractionThe combined aqueous layers were extracted with CH2Cl2
  4. dry with materialThe combined organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of the solvent
  7. customgave 90 mg of the crude material
  8. customThe material was purified by flash chromatography

Sources & evidence

ORD record
ord-cb0fbf6b6ac9473cb70bb3a5c561c16a
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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