HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Cis-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-methylcyclohexanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl Ester | HCID 11229944 | — |
| Reactant | 5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 57597747 | — |
| Reactant | 5-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine | HCID 67285321 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | Cis-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-methylcyclohexanecarboxamide | HCID 68007868 | — |
Reaction Steps
Pd(PPh3)4, sodium carbonate, DME/water, reflux; (b) meta-chloroperbenzoic acid, dichloromethane, rt; (c) 20a, tetrahydrofuran, 50° C.; (d) trifluoroacetic acid, dichloromethane, rt; (e) morpholine-4-carbonyl chloride, dimethylformamide, rt; (f) sodium methoxide, methanol, rt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829007B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-59024c44376b48a9819375bd1f094ec6 |
| Source note | uspto-grants-2014_09 |