Sodium Iodide → HCID 11663999, compound

HRID 1674498Notes

Reaction equation

HRID 1674498 reaction equation
Cl[CH2:2][CH2:3][CH:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([C:17]3[N:21]([CH3:22])[N:20]=[C:19]([CH3:23])[CH:18]=3)=[CH:16][C:9]=2[CH2:8][CH2:7]1)[CH3:5].[CH3:24][N:25]1[C:29]([C:30]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:31]=2[CH:32]=[CH:33][C:34]([CH3:40])=[N:35]3)=[N:28][NH:27][C:26]1=[S:41].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][N:21]1[C:17]([C:15]2[CH:14]=[CH:13][C:10]3[CH2:11][CH2:12][N:6]([CH:4]([CH3:5])[CH2:3][CH2:2][S:41][C:26]4[N:25]([CH3:24])[C:29]([C:30]5[CH:39]=[CH:38][CH:37]=[C:36]6[C:31]=5[CH:32]=[CH:33][C:34]([CH3:40])=[N:35]6)=[N:28][N:27]=4)[CH2:7][CH2:8][C:9]=3[CH:16]=2)=[CH:18][C:19]([CH3:23])=[N:20]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 446275704-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiol2×HCID 59864270HCID 59864270, compound2×

Product 1

HCID 11663999HCID 11663999, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 3-(3-chloro-1-methylpropyl)-7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (0.10 g) (intermediate 10) and 4-methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.093 g) (intermediate 7) in dimethylformamide (2 ml), at room temperature, sodium iodide (0.040 g) and anhydrous potassium carbonate were subsequently added. Then the reaction mixture was warmed to 70° C. and stirring continued for 3 h after which time the mixture was allowed to reach room temperature and the solvent evaporated under reduced pressure. The residue was treated with water (10 ml), extracted with ethyl acetate (20 ml). 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 7-(1,3-dimethyl-1H-pyrazol-5-yl)-3-(1-methyl-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 (0.040 g) as a pale yellow solid. This product was dissolved in dichloromethane (2 ml), and hydrochloridric acid was added dropwise (0.072 ml, 1M/ether), at room temperature. Following solvent evaporation gave the title compound (0.042 g) as a yellow solid.

Workup

  1. customto reach room temperature
  2. customthe solvent evaporated under reduced pressure
  3. additionThe residue was treated with water (10 ml)
  4. extractionextracted with ethyl acetate (20 ml)
  5. dry with materialThe organic phase was dried with sodium sulphate
  6. customafter evaporation the crude product
  7. customwas purified by chromatography on silica gel with 100-95% dichloromethane-methanol elution

Sources & evidence

ORD record
ord-8c2daa0b43fa4a33904460b8d2fec0e1
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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