1,2-Dichloroethane → 1-Ethyl-N-(2-hydroxy-1-methylethyl)(tetrahydro-2H-pyran-4 ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
Reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([OH:21])=O)[C:11](NC3CCOCC3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(Cl)CCl.C1[CH:27]=[CH:28][C:29]2[N:34](O)N=N[C:30]=2[CH:31]=1.[NH2:36][CH:37]([CH3:40])[CH2:38][OH:39].C(N(CC)CC)C.CN(C=[O:52])C>>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]([NH:36][CH:37]([CH3:40])[CH2:38][OH:39])=[O:21])[CH:11]=[C:6]2[C:5]([NH:34][CH:29]2[CH2:28][CH2:27][O:52][CH2:31][CH2:30]2)=[N:4]1)[CH3:2]Participants
7
Reactant 6
Product 1
Procedure
Intermediate 17 (0.1 g, 0.34 mmol), EDC (0.066 g, 0.34 mmol) and HOBT (0.05 g, 0.37 mmol) were suspended in DMF (2 ml) and stirred at room temperature under nitrogen for 15 min. 2-aminopropan-1-ol (0.026 g, 0.34 mmol) and triethylamine (0.036 g, 0.36 mmol) were added and the mixture was stirred at room temperature under nitrogen for 6 hours. Solvents were removed in vacuo and the residue partitioned between DCM and water. The organic layer was concentrated and applied to an SPE cartridge (aminopropyl, 5 g), which was eluted with methanol. Concentration in vacuo afforded Intermediate 34 (0.095 g). LCMS showed MH+=348, TRET=2.15 min.
Workup
- stirringthe mixture was stirred at room temperature under nitrogen for 6 hours
- customSolvents were removed in vacuo
- customthe residue partitioned between DCM and water
- concentrationThe organic layer was concentrated
- washwas eluted with methanol
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-96725450c4174c6c8f8625fbe42739db
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528148B2
Reaction notes
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