4-Methoxybenzenesulfonyl chloride → N-{2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-4-methoxy-N-methyl-benzenesulfonamide hydrochloride

HRID 553503Notes

Reaction equation

HRID 553503 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([Cl:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([N:26]3[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH:34][CH3:35])[CH2:28][CH2:27]3)=[N:22][CH:23]=[CH:24][N:25]=2)=[CH:16][CH:15]=1.N1CCOCC1>ClCCl>[ClH:12].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([N:26]3[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][N:34]([CH3:35])[S:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)(=[O:11])=[O:10])[CH2:30][CH2:31]3)=[N:22][CH:23]=[CH:24][N:25]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8083MorpholineHCID 67368348{2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

Product 1

HCID 67367044N-{2-[3'-(4-Fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-4-methoxy-N-methyl-benzenesulfonamide hydrochlorideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-methoxy-benzenesulfonyl chloride (0.110 g, 0.530 mmol, 1.1 eq.) in dichloromethane (4 mL). Add {2-[3′-(4-fluoro-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amine (0.150 g, 0.480 mmol, 1 eq.). Add morpholine, polymer-bound (0.220 g, 0.530 mmol, 1.1 eq.). Stir at room temperature for 2 hr. Purify by SCX chromatography (column washed with methanol and extracted with 7N NH3/MeOH) to afford the free base of the title compound (0.187 g, 80% yield). MS (loop): m/z=486.0 [M+H].

Workup

  1. customPurify by SCX chromatography (column washed with methanol and extracted with 7N NH3/MeOH)

Sources & evidence

ORD record
ord-25fca8240fbc44cdacc73df47ba40622
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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