Trimethylsilyl iodide → HCID 23398408, compound

HRID 1062444Notes

Reaction equation

HRID 1062444 reaction equation
C([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]([C:18]1[N:19]=[C:20]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])[N:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:22]=1)=[O:17])C1C=CC=CC=1.[Si](I)(C)(C)C>C(Cl)Cl.O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([N:21]2[CH:22]=[C:18]([C:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]3[OH:8])=[O:17])[N:19]=[C:20]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86591635HCID 86591635, compound

Product 1

HCID 23398408HCID 23398408, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1R, 2R)-2-(benzyloxy)cyclohexyl]-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxamide (Table entry 278, prepared according to the procedures described in Examples 13 and 14) (100 mg, 0.18 mmol) in CH2Cl2 (2 mL), TMSI (iodotrimethylsilane) (60 μL, 0.42 mmol) was added. The mixture was stirred at rt overnight, and diluted with water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC (EtOAc) to afford 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-1H-imidazole-4-carboxamide (56 mg, 67% yield) as a yellow solid: LC-MS m/z 464.3 (MH+), retention time 3.19 min (method 1); Rf=0.67 (EtOAc); 1H NMR (300 MHz, CDCl3) δ 1.16-1.30 (4H, m), 1.66-1.69 (2H, m), 1.98-2.02 (2H, m), 3.37-3.39 (1H, m), 3.70-3.80 (1H, m), 3.99-4.06 (1H, m), 6.96-7.37 (8H, m), 7.78 (1H, s).

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-fc8213a713a04c2bb1fb68f8246142fc
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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