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

HRID 553502Notes

Reaction equation

HRID 553502 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([N:27]3[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][NH:35][CH3:36])[CH2:29][CH2:28]3)=[N:23][CH:24]=[CH:25][N:26]=2)=[CH:17][CH:16]=1.N1CCOCC1>ClCCl>[ClH:11].[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:35]([CH2:34][CH2:33][N:30]2[CH2:29][CH2:28][N:27]([C:22]3[C:21]([C:18]4[CH:19]=[CH:20][C:15]([CH2:14][O:13][CH3:12])=[CH:16][CH:17]=4)=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:32][CH2:31]2)[CH3:36])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 67367004{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

Product 1

HCID 673677254-Fluoro-N-{2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-N-methyl-benzenesulfonamide hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-fluoro-benzenesulfonyl chloride (0.095 g, 0.49 mmol, 1.1 eq.) in dichloromethane (4 mL). Add {2-[3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amine (0.150 g, 0.440 mmol, 1 eq.). Add morpholine, polymer-bound (0.201 g, 0.490 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 (0.220 g, 100% yield). MS (loop): m/z=500.0 [M+H].

Workup

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

Sources & evidence

ORD record
ord-faf1e6f5a5094d0eb2f1d44ecc9f40d8
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

Loading…