Pyrrolidine → 1-{4-[2-Oxo-2-(1-Pyrrolidinyl)ethyl]phenyl}-3-(Trifluoromethyl)-4,5,6,7-Tetrahydro-1h-Indazole
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=2)[N:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>ClCCl>[O:20]=[C:19]([N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:3]([C:2]([F:23])([F:1])[F:22])=[N:4]2)=[CH:13][CH:14]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of {4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}acetic acid (113 mg, 0.35 mmol) in dichloromethane (4 ml) in a sarstedt tube was treated in one portion with solid 1,1′-carbonyldiimidazole (60 mg, 0.37 mmol). This mixture was shaken at room temperature for 30 minutes. Pyrrolidine (34 mg, 0.48 mmol) in dichloromethane (2 ml) was then added and the shaking continued for 16 hour at room temperature. The reaction mixture was washed with a mix of saturated sodium bicarbonate solution (4 ml) and brine (2 ml). The organic layer was then added to a 2 g SCX column and eluted with ethyl acetate (25 ml), the solvent removed under reduced pressure and the residue purified by mass directed auto-prep to give the title compound as a yellow oil (30 mg, 23%).
Workup
- waitthe shaking continued for 16 hour at room temperature
- washThe reaction mixture was washed with
- additiona mix of saturated sodium bicarbonate solution (4 ml) and brine (2 ml)
- additionThe organic layer was then added to a 2 g SCX column
- washeluted with ethyl acetate (25 ml)
- customthe solvent removed under reduced pressure
- customthe residue purified by mass
Sources & evidence
- ORD record
- ord-989001c34d1149c0ada39c4aaf894837
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642256B2
Reaction notes
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