o-Chlorophenylacetic acid → 2-(2-chlorophenyl)-1-(3-(pyridin-4-yl)-6,7-dihydro-1H-pyrazolo pyridin-5(4H)-yl)ethanone
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.CCN(C(C)C)C(C)C.CN(C(ON1[N:37]=[N:36][C:31]2[CH:32]=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[N:46]1[CH:51]=[CH:50][C:49]([C:52]2C3CNCCC=3NN=2)=[CH:48][CH:47]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:34]1[CH2:33][CH2:32][C:31]2[NH:36][N:37]=[C:52]([C:49]3[CH:50]=[CH:51][N:46]=[CH:47][CH:48]=3)[C:30]=2[NH:35]1)=[O:11]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of 2-(2-chlorophenyl)acetic acid (34 mg, 0.2 mmol) and DIEA (89 μA, 0.6 mmol) in DMF (1 ml) at 0° C., was added HATU (91 mg, 0.24 mmol). After stirring for 30 min, (3-(pyridin-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine hydrochloride was added. The reaction mixture was warmed to room temperature and continued stirring for 2 hour. Water was added and the reaction mixture was extracted with ethyl acetate (10 ml). The organic component was washed with water (5 ml) and brine (5 ml). After dry over sodium sulfate, solvent was removed under vacuum and the residue was purified using prep-HPLC to give the desired compound as white solid (20 mg). LC-MS found 353.22 (M+H).
Workup
- stirringcontinued stirring for 2 hour
- extractionthe reaction mixture was extracted with ethyl acetate (10 ml)
- washThe organic component was washed with water (5 ml) and brine (5 ml)
- dry with materialAfter dry over sodium sulfate, solvent
- customwas removed under vacuum
- customthe residue was purified
Sources & evidence
- ORD record
- ord-6d3418457491406a8615bdf96584ecc2
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242981B2
Reaction notes
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