Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Morpholine, 4-(chloroacetyl)- | HCID 74040 | — |
| Reactant | Isothiazolo(5,4-b)pyridin-3(2H)-one, 4,6-dimethyl- | HCID 173760 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67951154 | HCID 67951154 | 9.3% |
Reaction Steps
Pyridinothiazolone 4 (200 mg, 1.22 mmol), was treated with 2-chloro-1-morpholinoethanone (225 mg, 1.25 mmol) and Et3N (370 mg, 3.66 mmol) in anhydrous CH2Cl2 (25 mL) at reflux (40° C.) for 24 h, and then washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1) to give the title compound (35 mg, 9% yield) in addition to the main N-alkylation product 19 (55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09278982B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-cc79e810608d4c4c9b976b1139d63eac |
|---|
| Source note | uspto-grants-2016_03 |
|---|
