HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 178425144, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 6-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide | HCID 56597425 | — |
| Reactant | HCID 178514825 | HCID 178514825 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 178425144 | HCID 178425144 | — |
Reaction Steps
The title compound was prepared in the same manner as described in example 74 using 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 1H-1,2,3-benzotriazol-5-ylboronic acid (39.7 mg, 0.243 mmol), DMSO (2 mL), sodium carbonate (0.281 mL, 0.562 mmol) and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 22 mg (26%). LCMS E-S (M+H)=457.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (d, 6 J=6.4 Hz, H), 2.14 (s, 3H), 2.24 (s, 3H), 4.43 (d, J=4.3 Hz, 2H), 5.31-5.46 (m, 1H), 5.91 (s, 1H), 8.07 (br. s., 1H), 8.34 (s, 1H), 8.41 (m, 2H), 8.85 (br. s., 1H), 9.02 (br. s., 1H), 11.59 (br. s., 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637509B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-aeb6d1246f724137bccff1bb951aedd7 |
| Source note | uspto-grants-2014_01 |