HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroacetyl chloride → 2-Chloro-N-{4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]benzyl}-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | [6-(4-Aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine | HCID 59756727 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-Chloro-N-{4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]benzyl}-acetamide | HCID 69181468 | — |
Reaction Steps
A mixture of 0.21 g (0.6 mmol)[6-(4-aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine and 94 μl (0.67 mmol) triethylamine in 5 ml dry THF is treated dropwise with a solution of chloro-acetyl chloride (51 μl, 0.64 mmol) in 0.5 ml of dry THF at RT. After stirring for 30 min small amounts of insoluble material is removed by filtration and the filtrate is evaporated. The residue is purified by flash chromatography using ethyl acetate/methanol 100:2 to 100:4 as eluent. The title compound is obtained as light brown solid HPLC tR=9.36 min; MS-ES+: (M+H)+=420.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07390805B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-65a3a94cbd38480da95c05b1e2c2ee43 |
| Source note | uspto-grants-2008_06 |