Triethylamine → HCID 118378949, compound
Reaction equation
[I:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=O)=[C:6]2[CH:5]=[C:4]([CH3:14])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[C@H:47]12[CH2:53][C@H:50]([NH:51][CH2:52]1)[CH2:49][O:48]2>CN(C=O)C.O>[C@H:47]12[CH2:53][C@H:50]([N:51]([C:11]([C:10]3[CH:9]=[N:8][N:7]4[C:2]([I:1])=[CH:3][C:4]([CH3:14])=[CH:5][C:6]=34)=[O:13])[CH2:52]1)[CH2:49][O:48]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 7-iodo-5-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid (500 mg) in DMF (10 mL) were added HATU (755 mg) and triethylamine (0.531 mL), and the mixture was stirred at room temperature for 3 min. To the reaction mixture was added (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride (247 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (300 mg).
Workup
- stirringthe mixture was stirred at room temperature for 1 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium bicarbonate solution and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ed72e3d5ca0b43d4885133c9fb2644cf
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296746B2
Reaction notes
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