Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:11]=[C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)[O:9][N:8]=1.[C:17]([O:21][C:22]([NH:24][C:25]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=NS(C(F)(F)F)(=O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:38]([O:37][C:35]([NH:34][C:25]([N:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[C:10]1[O:9][N:8]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:11]=1)=[N:24][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])=[O:36])([CH3:41])([CH3:40])[CH3:39]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-[3-(Pyrid-2-yl)isoxazol-5-yl]pyrrolidine (Method 12) (1.5 g, 7 mmol) was added to a solution of N,N′-di(tertbutyloxycarbonyl)-N″-(trifluoromethylsulphonyl)guanidine (2.59 g, 6.6 mmol) and triethylamine (0.975 ml) in DCM and the mixture stirred at ambient temperature for 8 hours. The mixture was then washed with water, dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 98:2) to give the title compound (2.3 g, 70%).
Workup
- washThe mixture was then washed with water
- dry with materialdried (MgSO4)
- customthe volatiles removed by evaporation
- customThe residue was purified by chromatography on silica gel eluting with DCM/methanol (100:0 increasing in polarity to 98:2)
Sources & evidence
- ORD record
- ord-aac05e9011ea4aad9d3f54f9b185eb23
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579349B2
Linked notes
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