Triethylamine → 1-[4-(4-Fluorophenyl)-3,6-dihydropyridin-1(2H)-yl]sulfonyl-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate

HRID 724730Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([N:17]3[CH:21]=[CH:20][N:19]=[C:18]3[CH3:22])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[CH2:23](N(CC)CC)C.[F:30][C:31]([F:38])([F:37])[S:32]([O:35]C)(=[O:34])=[O:33]>C(Cl)Cl>[F:30][C:31]([F:38])([F:37])[S:32]([O-:35])(=[O:34])=[O:33].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([S:14]([N:17]3[CH:21]=[CH:20][N+:19]([CH3:23])=[C:18]3[CH3:22])(=[O:15])=[O:16])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(4-fluorophenyl)-1-[(2-methyl-1h-imidazol-1-yl)sulfonyl]-1,2,3,6-tetrahydropyridine (125 mg, 389 μmol), triethylamine (54 μL, 390 μmol) and methylene chloride (5.4 mL) was stirred at 0° C. and slowly added methyl trifluoromethanesulfonate (43 μL, 390 μmol). The reaction mixture was stirred at 0° C. for 1 h. The resulting precipitate was filtered to yield the desired product (80 mg, 42%). MF=C17H19F4N3O5S2; LCMS found for C16H20FN3O2S(M+H)+: m/z=336.

Workup

filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-0246250a7efe4ceeac5964c1ca429ffb
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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