2-butyl-1H-imidazole → HCID 67132951, compound

HRID 659681Notes

Reaction equation

Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:11][C:10]=2[S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH:6]=[CH:7][CH:8]=1.[CH2:26]([C:30]1[NH:31][CH:32]=[CH:33][N:34]=1)[CH2:27][CH2:28][CH3:29]>O1CCOCC1>[CH2:26]([C:30]1[N:31]([CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[CH:13]=[C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:11][C:10]=3[S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH:6]=[CH:7][CH:8]=2)[CH:32]=[CH:33][N:34]=1)[CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (70 mg, 0.158 mmol; see Example 1(e)) in dioxane (2.0 mL) was added 2-butylimidazole (58.7 mg, 0.473 mmol) and the reaction mixture was stirred for 1 h at 80° C. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography using MeOH:CH2Cl2 (5:95) as eluent to give the sub-title compound in 55% yield as a colourless syrup (42.1 mg, 0.087 mmol).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-f5551585900d4a62879f15cc1e5ae587
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080571B2

Reaction notes

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