HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → 4-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-(Dimethylamino)benzoyl chloride | HCID 4400782 | — |
| Reactant | 4-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide | HCID 86730983 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Pyridine methylene chloride | HCID 21875418 | — |
| Product | 4-{4-[3-(4-Dimethylamino-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide | HCID 71230911 | — |
Reaction Steps
To a solution of aniline Intermediate 6 (84 mg, 0.213 mmol) in DCM/pyridine (2:1, 30 ml) were added DIPEA (0.372 ml, 2.13 mmol), 4-dimethylaminobenzoyl chloride (43 mg, 0.234 mmol), and DMAP (2.6 mg, 0.021 mmol). The resulting mixture was stirred at room temperature for 75 hrs. The solvents were removed in vacuo and the resulting mixture was purified by reversed phase HPLC (MeCN/H2O) to afford Example 15.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09233111B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-aaee8eeac4e4474d826b1d814f3c5335 |
| Source note | uspto-grants-2016_01 |