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.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.ClCCl.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:29]([C:26]3[CH:25]=[CH:24][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[CH:28][CH:27]=3)(=[O:30])=[O:31])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (117 mg, 0.5 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with a solution 4-(2-thienyl)benzenesulfonyl chloride (WO 9827069) (143 mg, 0.55 mmol) in dichloromethane (2 ml). The solution was stirred at room temperature for 24 hours, quenched with methanol (2 ml) and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water (×3). The organic phase was applied to a SCX cartridge (Varian bond-elute, 5 g) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane) to afford the title product (E11). MS (ES+) m/e 458 [M+H]+.
Workup
- customquenched with methanol (2 ml)
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in dichloromethane
- washwashed with water (×3)
- washwashed with methanol and 2M ammonia in methanol
- concentrationThe combined basic fractions were concentrated in vacuo
- customthe resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane)
Sources & evidence
- ORD record
- ord-c605a5a7a06b49218e76290c326b7258
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381728B2
Linked notes
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