Triethylamine → HCID 86726888, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.[NH:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1.C(N(CC)CC)C>C(O)(C)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1Participants
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 3-bromo-4-chloro-5-nitropyridine (from Ark Pharm, 0.050 g, 0.21 mmol), benzyl (3S)-piperidin-3-ylcarbamate (0.059 g, 0.25 mmol), and triethylamine (0.088 mL, 0.63 mmol) in isopropyl alcohol (0.8 mL) was heated at 90° C. in a sealed vial for 16 h. The reaction mixture was diluted with EtOAc (40 mL) and water (3 mL). The layers were separated and the organic layer was washed with water (3×3 mL) and the combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.084 g). The crude product was used without further purification in the subsequent reaction. LCMS (ESI) calc. for C18H20BrN4O4[M+H]+: m/z=435.1. found 435.0/437.0.
Workup
- customThe layers were separated
- washthe organic layer was washed with water (3×3 mL)
- extractionthe combined aqueous phases were extracted with EtOAc (3 mL)
- washThe combined organic layers were washed with brine (3 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-99ea7291633e465eb1d7b9e2ad710623
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278950B2
Reaction notes
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