Pyridine → 2-(4-chlorophenyl)-N-methoxy-N-methyl-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxamide

HRID 1353011Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CN(C)C=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([C:27]3[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=3)[CH:21]=[C:22]([C:24](O)=[O:25])[N:23]=2)=[CH:15][CH:14]=1.[CH3:37][NH:38][O:39][CH3:40].Cl.N1C=CC=CC=1>C(#N)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]([C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=3)[CH:21]=[C:22]([C:24]([N:38]([O:39][CH3:40])[CH3:37])=[O:25])[N:23]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalyl chloride (0.34 g, 2.65 mmole) in 5 ml acetonitrile was added to 16 ml acetonitrile containing dimethylformamide (0.25 g, 3.46 mmole) cooled to 0° C. After 15 minutes, 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxylic acid from step 1 (1.0 g, 2.65 mmole) was added with 20 ml acetonitrile. After warming to room temperature N,0-dimethylhydroxylamine HCl (0.28 g, 2.92 mmole) and pyridine (0.42 g, 5.31 mmole) were added and the mixture was stirred at room temperature for three days. The reaction mixture was concentrated to give an oily solid. The amide was purified by silica gel chromatography: Anal. Calc'd. C19H15N3O4SCl (419.89); C, 54.35; H. 4.32; N, 10 10.01. Found: C, 53.96; H, 4.30; N, 9.68.

Workup

additionwere added
concentrationThe reaction mixture was concentrated
customto give an oily solid
customThe amide was purified by silica gel chromatography

Sources & evidence

ORD record: ord-a0b9f10f15f24a5d99270f80cf512128
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220770B2

Reaction notes

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