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

HRID 553505Notes

Reaction equation

HRID 553505 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][CH3:23])[CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.N1CCOCC1.[CH3:30][N:31]1[C:35]([S:36]([Cl:39])(=[O:38])=[O:37])=[CH:34][N:33]=[C:32]1[CH3:40]>ClCCl>[ClH:39].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][N:22]([CH3:23])[S:36]([C:35]4[N:31]([CH3:30])[C:32]([CH3:40])=[N:33][CH:34]=4)(=[O:38])=[O:37])[CH2:18][CH2:19]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 27362581,2-dimethyl-1H-imidazole-5-sulfonyl chlorideHCID 67368348{2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

Product 1

HCID 673674752,3-Dimethyl-3H-imidazole-4-sulfonic acid {2-[3'-(4-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve {2-[3′-(4-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amine (0.111 g, 0.352 mmol) in dichloromethane (4 mL). Add resin-bound morpholine (0.155 g, 0.387 mmol) followed by 1,2-dimethylimidazole-5-sulfonyl chloride (0.075 g, 0.387 mmol) and shake at ambient temperature for 72 hr. Filter, concentrate and purify (SCX chromatography, followed by silica gel chromatography, eluting with 100:0 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 (118 mg, 71%).

Workup

  1. filtrationFilter
  2. concentrationconcentrate
  3. custompurify (SCX chromatography
  4. washeluting with 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-01cbc4e6ac734292a1b07b2d32304839
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

Loading…