HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → N-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | 3-[3-({1-[2-(Benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamide | HCID 66689500 | — |
| Solvent | Water | HCID 962 | — |
| Product | N-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide | HCID 66689180 | — |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
A solution of 3-[3-({1-[2-(benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamide (Example 330g, 2.23 g) dissolved in DCM (30 mL) was treated with boron tribromide (8.43 mL of a 1M solution in DCM) at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was diluted with water (200 mL), and extracted with dichloromethane (250 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was triturated with diethyl ether (50 mL) to afford the subtitle compound (1.760 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889692B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-f17b71feab764badbf043d980742ccff |
| Source note | uspto-grants-2014_11 |