Dimethylformamide → N'-(Cyclobutylcarbonyl)-1-ethyl(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide
Reaction equation
CN(C(O[N:9]1N=N[C:11]2[CH:12]=C[CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH:32]1([C:36]([OH:38])=O)[CH2:35][CH2:34][CH2:33]1.Cl.Cl.[CH2:41]([N:43]1[C:47]2=[N:48][CH:49]=[C:50]([C:59]([NH:61][NH2:62])=[O:60])[C:51](NC3CCOCC3)=[C:46]2[CH:45]=[N:44]1)[CH3:42].CN(C=[O:67])C>>[CH:32]1([C:36]([NH:62][NH:61][C:59]([C:50]2[CH:51]=[C:46]3[C:45]([NH:9][CH:10]4[CH2:11][CH2:12][O:67][CH2:14][CH2:15]4)=[N:44][N:43]([CH2:41][CH3:42])[C:47]3=[N:48][CH:49]=2)=[O:60])=[O:38])[CH2:33][CH2:34][CH2:35]1Participants
6
Reactant 5
Product 1
Conditions
- Temperature
- 20 °C
Procedure
TBTU (0.050 g, 0.15 mmol) and diisopropylethylamine (0.04 ml, 0.26 mmol) in DMF (0.5 ml) was added to cyclobutylcarboxylic acid (RYCOOH, 0.015 g, 0.15 mmol). The reaction mixture was stirred for 40 minutes at 20° C. A mixture of Intermediate 19 (0.045 g, 0.13 mmol) and diisopropylethylamine (0.04 ml, 0.26 mmol) in DMF (0.5 ml) was added and the reaction mixture stirred for 18 h. The solvent was removed in vacuo and the residue applied to a SPE cartridge (aminopropyl, 2 g). The cartridge was eluted with methanol to afford Intermediate 65 (0.052 g). LCMS showed MH+=387; TRET=2.28 min.
Workup
- additionwas added
- stirringthe reaction mixture stirred for 18 h
- customThe solvent was removed in vacuo
- washThe cartridge was eluted with methanol
Sources & evidence
- ORD record
- ord-fd88d79a964d457d9816ed394ea7e3fa
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528148B2
Reaction notes
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