N-bromobutanimide → HCID 60052517, compound

HRID 1062452Notes

Reaction equation

HRID 1062452 reaction equation
[CH2:1]([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][CH:33]=[CH:32][C:31]=2[Cl:36])[N:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:22]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:37]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([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][CH:33]=[CH:32][C:31]=2[Cl:36])[N:21]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:22]=1[Br:37])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69745357HCID 69745357, compound

Product 1

HCID 60052517HCID 60052517, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-[(1S,2S)-2-(benzyloxy)cyclohexyl]-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxamide (Table entry 276) (198 mg, 0.380 mmol) and N-bromosuccinimide (88 mg, 0.49 mmol) in dimethylformamide (5 mL) was stirred at 75° C. for 3 days. The solution was purified by preparative HPLC to give N-[(1S,2S)-2-(benzyloxy)cyclohexyl]-5-bromo-2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxamide as a white solid (196 mg, 86%). LC-MS m/z 598.1 (MH+), retention time 3.72 min (method 2).

Workup

  1. customThe solution was purified by preparative HPLC

Sources & evidence

ORD record
ord-1a8ff173472f4193ad0bea354cb744ee
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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