4-Methylmorpholine → N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-5-(2-pyridinyl)-2-thiophenesulfonamide
Reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[NH2:12])[CH2:3]1.CN1CCOCC1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[S:35][C:34]([S:36](Cl)(=[O:38])=[O:37])=[CH:33][CH:32]=1>ClCCl>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([NH:12][S:36]([C:34]3[S:35][C:31]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][N:25]=4)=[CH:32][CH:33]=3)(=[O:37])=[O:38])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (100 mg, 0.42 mmol) in dichloromethane (10 ml) was stirred with morpholinomethyl-polystyrene HL resin (320 mg, 4 mmol/g loading, 1.28 mmol) at ambient temperature. 5-(2-Pyridinyl)-2-thiophenesulfonyl chloride (110 mg, 0.4 mmol) was added and the mixture stirred for 18 hours. Argopore-trisamine scavenger resin (100 mg, 4 mmol/g loading, 0.4 mmol) was then added and the mixture stirred for a further 30 minutes. The resin was removed by filtration, washed with dichloromethane and the filtrate concentrated in vacuo. The residue was purified by column chromatography (1:19 2M ammonia in methanol: dichloromethane) to afford the title product (El). MS (ES+) 459 [M+H]+.
Workup
- stirringthe mixture stirred for a further 30 minutes
- customThe resin was removed by filtration
- washwashed with dichloromethane
- concentrationthe filtrate concentrated in vacuo
- customThe residue was purified by column chromatography (1:19 2M ammonia in methanol: dichloromethane)
Sources & evidence
- ORD record
- ord-91b6620d1309474c816b0a56279d263f
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381728B2
Reaction notes
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