Triethylamine → Ethyl 4-(4-fluorophenylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 490875Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(O)C>[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=23)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Intermediate 1 (0.051 g) and 4-fluoroaniline (0.024 g) were suspended in ethanol (2 ml) and triethylamine (0.14 ml) was added. The mixture was stirred under nitrogen and heated at 80° C. for 16 h. After cooling to room temperature, ethanol was removed by evaporation under a stream of nitrogen and the residue partitioned between DCM and water. The organic layer was loaded directly onto an SPE cartridge (silica, 5 g) and eluted sequentially with; (i) DCM, (ii) DCM: Et2O (2:1), (iii) DCM:Et2O (1:1), (iv) Et2O, (v) EtOAc, (vi) MeOH. Fractions containing desired material were combined and concentrated in vacuo to afford Intermediate 6 (0.077 g). LCMS showed MH+=328; TRET=3.36 min.

Workup

temperatureAfter cooling to room temperature
customethanol was removed by evaporation under a stream of nitrogen
customthe residue partitioned between DCM and water
washeluted sequentially with
additionFractions containing desired material
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0a863f7e7e004a798d97aa5cdca56e6d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528148B2

Reaction notes

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