Cyclohexyl isocyanate → 4,5-bis(4-chlorophenyl)-N-cyclohexyl-1H-imidazole-2-carboxamide

HRID 2101709Notes

Reaction equation

[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[CH:19][N:20](COCC[Si](C)(C)C)[C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:13][CH:12]=1>>[CH:1]1([NH:7][C:8]([C:19]2[NH:20][C:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=3)[N:18]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 18502Cyclohexyl isocyanate

HCID 22066067HCID 22066067, compound

Product 1

HCID 101124434,5-bis(4-chlorophenyl)-N-cyclohexyl-1H-imidazole-2-carboxamide

Procedure

Using essentially the same procedure as Example 25, Step B-C, but using cyclohexyl isocyanate (0.027 mL, 0.21 mmol) in Step B, 4,5-di-(4-chlorophenyl)-1-(2-(trimethylsilyl)ethoxymethyl)imidazole (36 mg, 0.086 mmol) from Example 25, Step A was converted to the SEM intermediate and then to the title compound with TBAF.

Sources & evidence

ORD record: ord-bffd224793bd4fd29108a04362f8b892
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572785B2

Reaction notes

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