Sodium Iodide → 7-(1,3-dimethyl-1H-pyrazol-5-yl)-3-(3-((4-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazol-3-yl)thio)propyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 1674492Notes

Reaction equation

HRID 1674492 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1.Cl[CH2:20][CH2:21][CH2:22][S:23][C:24]1[N:25]([CH3:40])[C:26]([C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][C:33]([CH3:39])=[N:34]3)=[N:27][N:28]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:1][N:2]1[C:6]([C:7]2[CH:17]=[CH:16][C:10]3[CH2:11][CH2:12][N:13]([CH2:20][CH2:21][CH2:22][S:23][C:24]4[N:25]([CH3:40])[C:26]([C:29]5[CH:38]=[CH:37][CH:36]=[C:35]6[C:30]=5[CH:31]=[CH:32][C:33]([CH3:39])=[N:34]6)=[N:27][N:28]=4)[CH2:14][CH2:15][C:9]=3[CH:8]=2)=[CH:5][C:4]([CH3:18])=[N:3]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 251050497-(1,3-Dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine2×HCID 251050505-(5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl)-2-methylquinoline2×

Product 1

HCID 115846607-(1,3-dimethyl-1H-pyrazol-5-yl)-3-(3-((4-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazol-3-yl)thio)propyl)-2,3,4,5-tetrahydro-1H-3-benzazepineYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (4 g) (intermediate 3) in dimethylformamide, at room temperature, 5-{5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}-2-methylquinoline (intermediate 8) (6.8 g), sodium iodide (3.06 g) and anhydrous potassium carbonate (2.82 g) were subsequently added and the reaction mixture was warmed to 60° C. and kept reacting for 24 h. After allowing the reaction mixture to reach room temperature, water (70 ml) was added and the reaction mixture was extracted twice with ethyl acetate (50 ml×2). The organic phase was dried with sodium sulphate and after evaporation the crude product was purified by chromatography on silica gel with 100-95% dichloromethane-methanol elution to give the title compound (3.3 g) as a pale yellow solid.

Workup

  1. customto reach room temperature
  2. extractionthe reaction mixture was extracted twice with ethyl acetate (50 ml×2)
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. customafter evaporation the crude product
  5. customwas purified by chromatography on silica gel with 100-95% dichloromethane-methanol elution

Sources & evidence

ORD record
ord-a7f54671d70e4eea9d9e95f43beb51d4
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

Loading…