Water → HCID 23398407, compound

HRID 1062445Notes

Reaction equation

HRID 1062445 reaction equation
C([O:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:14][C:15]([C:17]1[N:18]=[C:19]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[Cl:36])[N:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH:21]=1)=[O:16])C1C=CC=CC=1.[Si](I)(C)(C)C.O>C(Cl)Cl>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:20]2[CH:21]=[C:17]([C:15]([NH:14][C@H:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]3[OH:8])=[O:16])[N:18]=[C:19]2[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[Cl:36])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 86591636HCID 86591636, compound

Product 1

HCID 23398407HCID 23398407, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1S, 2S)-2-(benzyloxy)cyclopentyl]-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxamide (Table entry 282, prepared according to the procedures described in Examples 13 and 14) (119 mg, 0.22 mmol) in CH2Cl2 (4 mL), TMSI (0.2 mL, 1.4 mmol) was added. The mixture was stirred at rt overnight, and diluted by 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-[(1S, 2S)-2-hydroxycyclopentyl]-1H-imidazole-4-carboxamide (80 mg, 82% yield) as a white foam: LC-MS m/z 450.0 (MH+), retention time 3.24 min (method 1); Rf=0.45 (50% EtOAc in hexane); 1H NMR (300 MHz, CDCl3) δ 1.22-2.24 (6H, m), 3.97-4.15 (2H, m), 7.03-7.42 (7H, m), 7.86 (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-95589e5d3be64fd7a3b0c6dd6053a936
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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