Sodium Iodide → HCID 67360031, compound

HRID 1668642Notes

Reaction equation

HRID 1668642 reaction equation
Cl.[Br:2][C:3]1[C:13]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[C:6](C(C)CC[Cl:17])=[C:5]2[N:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[O:21][C:4]=12.[CH3:26][N:27]1[C:31]([C:32]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:33]=2[CH:34]=[CH:35][C:36]([CH3:42])=[N:37]3)=[N:30][NH:29][C:28]1=[S:43].C(N([CH2:49][CH3:50])CC)C.[I-].[Na+].[C:53](OCC)(=O)[CH3:54]>CN(C=O)C>[ClH:17].[Br:2][C:3]1[C:13]2[CH2:12][CH2:11][N:10]([CH:49]([CH3:50])[CH2:53][CH2:54][S:43][C:28]3[N:27]([CH3:26])[C:31]([C:32]4[CH:41]=[CH:40][CH:39]=[C:38]5[C:33]=4[CH:34]=[CH:35][C:36]([CH3:42])=[N:37]5)=[N:30][N:29]=3)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]2[N:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[O:21][C:4]=12

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 446275704-methyl-5-(2-methyl-5-quinolinyl)-4H-1,2,4-triazole-3-thiolHCID 86638058HCID 86638058, compound

Product 1

HCID 67360031HCID 67360031, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 10-bromo-(3-chloro-1-methyl-propyl)-2-trifluoromethyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5h][3]benzazepine hydrochloride (195 mg), 4-methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (130 mg), triethylamine (0.148 ml) and sodium iodide (63 mg) in dry DMF (0.8 ml) was heated at 70° C. for 24 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with 5% NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was purified on silica gel (DCM/MeOH/NH4OH: 100/1.5/0.15). The obtained product was treated with HCl (1N/ether) affording the title compound as a colourless slightly hygroscopic solid (46 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with 5% NaHCO3
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (DCM/MeOH/NH4OH: 100/1.5/0.15)
  6. additionThe obtained product was treated with HCl (1N/ether)

Sources & evidence

ORD record
ord-5ab6aa9ab23649759e0f335d61ffcbe6
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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