HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → N-(1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethyl)-9H-purine-6-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine | HCID 67300976 | — |
| Reactant | HCID 178419477 | HCID 178419477 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | N-(1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl}ethyl)-9H-purine-6-amine | HCID 178495643 | — |
Reaction Steps
A mixture of 6-bromo-9H-purine (0.0174 g, 0.0876 mmol), 1-{5-chloro-8-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]quinolin-7-yl]ethanamine (0.014 g, 0.044 mmol), and N,N-diisopropylethylamine (0.01525 mL, 0.0876 mmol) in ethanol (0.1 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resultant residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/minute) to give the product as a mixture of diastereoisomers (bis-TFA salts). LCMS calculated for C22H25ClN7O(M+H)+: m/z=438.2; found: 438.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680108B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-542139dd44bb4746bd9193dc18bed8be |
| Source note | uspto-grants-2014_03 |