Triethylamine → 1,2-Dimethyl-1H-imidazole-4-sulfonic acid {2-[3'-(2-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochloride

HRID 553506Notes

Reaction equation

HRID 553506 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][CH3:23])[CH2:16][CH2:15]2)=[N:10][CH:11]=[CH:12][N:13]=1.C(N(CC)CC)C.[CH3:31][N:32]1[CH:36]=[C:35]([S:37]([Cl:40])(=[O:39])=[O:38])[N:34]=[C:33]1[CH3:41]>ClCCl>[ClH:40].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][N:22]([CH3:23])[S:37]([C:35]3[N:34]=[C:33]([CH3:41])[N:32]([CH3:31])[CH:36]=3)(=[O:39])=[O:38])[CH2:18][CH2:19]2)=[N:10][CH:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27362561,2-Dimethylimidazole-4-sulfonyl chlorideHCID 67368864{2-[3'-(2-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

Product 1

HCID 673682311,2-Dimethyl-1H-imidazole-4-sulfonic acid {2-[3'-(2-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve {2-[3′-(2-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amine (0.059 g, 0.190 mmol) in dichloromethane (5 mL). Add triethylamine (29 μL, 0.209 mmol) followed by 1,2-dimethyl-1H-imidazole-4-sulfonyl chloride (0.041 g, 0.209 mmol) and stir at ambient temperature for 72 hr. Concentrate under reduced pressure and purify (silica gel chromatography, eluting with 20:80 to 0:100 hexanes:ethyl acetate, then 10:90 methanol:ethyl acetate, then 20:80 methanol:ethyl acetate) to give the free base of the title compound (71 mg, 79%).

Workup

  1. concentrationConcentrate under reduced pressure
  2. custompurify (silica gel chromatography
  3. washeluting with 20:80 to 0:100 hexanes

Sources & evidence

ORD record
ord-bd2343fcb0134771882f15329b5f632b
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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