HCID 118080519, compound → HCID 118080513, compound

HRID 1485782Notes

Reaction equation

HRID 1485782 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:17]3[CH:18]=[N:19][N:20]([CH:22]4[CH2:24][CH2:23]4)[CH:21]=3)=[C:11]([N+:14]([O-])=O)[CH:12]=2)[N:7]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]>C(O)C.O.Cl.[Fe]>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:17]3[CH:18]=[N:19][N:20]([CH:22]4[CH2:24][CH2:23]4)[CH:21]=3)=[C:11]([NH2:14])[CH:12]=2)[N:7]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

Participants

6

Reactant 1

HCID 118080519HCID 118080519, compound

Product 1

HCID 118080513HCID 118080513, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Iron powder (1.010 g, 18.09 mmol) was added to a solution of isopropyl (S)-4-acetyl-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-6-nitro-3,4-dihydroquinoxaline-1(2H)-carboxylate (0.86 g, 1.81 mmol) in ethanol (12 mL) and water (2.4 mL). 1 N aqueous HCl (1 drop) was added, and the reaction was heated at 90° C. for 2 h. The mixture was cooled to rt and filtered through a pad of Celite, washing with ethanol. The filtrate was concentrated, and ethyl acetate was added. The solution was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford isopropyl (S)-4-acetyl-6-amino-7-(1-cyclopropyl-1H-pyrazol-4-yl)-3-methyl-3,4-dihydroquinoxaline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 398 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through a pad of Celite
  3. washwashing with ethanol
  4. concentrationThe filtrate was concentrated
  5. additionethyl acetate was added
  6. washThe solution was washed with saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by mass
  11. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-5ff2093a1b1a4fcdb7ed8bd3d9a0dbce
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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