Trimethylsilyl iodide → HCID 44425219, compound

HRID 1062453Notes

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

Participants

Reactant 2

HCID 85247Trimethylsilyl iodide

HCID 60052517HCID 60052517, compound

Product 1

HCID 44425219HCID 44425219, compound

Procedure

As described previously for Example 35, N-[(1S,2S)-2-(benzyloxy)cyclohexyl]-5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxamide (Example 43) was de-benzylated by treatment with iodotrimethylsilane to give 5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-[(1S,2S)-2-hydroxycyclohexyl]-1H-imidazole-4-carboxamide. LC-MS m/z 508.1 (MH+), retention time 2.96 min (method 2). 1H NMR (CD2Cl2, 400 MHz) δ 7.43 (d, 1H, Ph), 7.27 (m, 5H, Ph), 7.06 (m, 2H, Ph), 3.70 (m, 1H, CHOH), 3.44 (m, 1H, CHN), 1.95 (m, 2H, cyclohexane), 1.64 (m, 2H, cyclohexane), 1.24 (m, 4H, cyclohexane).

Sources & evidence

ORD record: ord-f885acfdaec04e4e8e49264ec5d23b5a
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960601B2

Reaction notes

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