Triethylamine → HCID 118080544, compound

HRID 1485790Notes

Reaction equation

HRID 1485790 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[C:11]([N+:14]([O-])=O)[CH:12]=2)[N:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2].C(N(CC)CC)C>[Pd].CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[N:7]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 118080532HCID 118080532, compound

Product 1

HCID 118080544HCID 118080544, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of isopropyl (S)-4-acetyl-7-bromo-3-methyl-6-nitro-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.23 g, 0.575 mmol), methanol (23 mL), triethylamine (0.80 mL, 0.575 mmol) and palladium on carbon (10 wt %, 23 mg) was added to a Parr bottle, and the mixture was shaken at room temperature for 3 h under a hydrogen atmosphere (30 psi). The mixture was filtered through Celite and the filter cake was washed with methanol. The filtrate was concentrated to afford isopropyl (S)-4-acetyl-6-amino-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.167 g, 100%). MS (ESI, pos. ion) m/z 314 [M+Na]+.

Workup

  1. additionwas added to a Parr bottle
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter cake was washed with methanol
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-03916cbd724f4fdca73a8b25ed395d9c
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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