Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 86717465 | HCID 86717465 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86717569 | HCID 86717569 | 65% |
Reaction Steps
A mixture of ((2R,5S)-5-{2-[(1R)-1-hydroxyethyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl}tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate (25 mg, 0.052 mmol) and sodium azide (5.0 mg, 0.077 mmol) in DMF (0.5 mL) was stirred at 60° C. overnight. After cooling to room temperature, the mixture was diluted with methanol and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give desired product (12 mg, 65%). LCMS calculated for C16H19N6O2S (M+H)+: m/z=359.1. Found: 359.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181271B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-d1d71c70f8b349ef807f3932bf77e2ab |
|---|
| Source note | uspto-grants-2015_11 |
|---|