Pyrrolidine → 1-(Pyrrolidin-1-yl)-2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)ethan-1-one
Reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([O:18][CH2:19][C:20]([OH:22])=O)[C:14]=3[CH:23]=2)=[CH:6][CH:5]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[N:26]1([C:20](=[O:22])[CH2:19][O:18][C:15]2[C:14]3[CH:23]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:24])=[CH:9][CH:8]=4)[CH:11]=[CH:12][C:13]=3[O:17][N:16]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetic acid (50 mg, 0.142 mmol) was dissolved in 3 mL DMF. Pyrrolidine (30 mg, 0.425 mmol) was added followed by addition of HATU (81 mg, 0.212 mmol). The mixture was stirred at ambient temperature overnight, then diluted with 60 mL ethyl acetate, washed with water and brine, and evaporated. The product was purified on 12 g silica gel with 0-100% ethyl acetate in hexane followed by recrystallization from acetonitrile/water to give the title compound (30 mg, 0.073 mmol).
Workup
- washwashed with water and brine
- customevaporated
- customThe product was purified on 12 g silica gel with 0-100% ethyl acetate in hexane
- customfollowed by recrystallization from acetonitrile/water
Sources & evidence
- ORD record
- ord-3d20dee5a19b4a82ad82bd3ee001c403
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416115B2
Reaction notes
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