Hydrochloric Acid → phenyl (S)-4-acetyl-3-methyl-7-(4-(piperazine-1-carbonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate

HRID 1485754Notes

Reaction equation

HRID 1485754 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:34]=[CH:33][C:17]([C:18]([N:20]4[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]4)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[NH:7][CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:46]([O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:47].Cl>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([N:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)=[O:19])=[CH:33][CH:34]=3)=[CH:11][CH:12]=2)[N:7]([C:46]([O:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:47])[CH2:6][C@@H:5]1[CH3:35])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 118079960HCID 118079960, compound

Product 1

HCID 118080521phenyl (S)-4-acetyl-3-methyl-7-(4-(piperazine-1-carbonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A reaction vial was charged with (S)-tert-butyl 4-(4-(1-acetyl-2-methyl-1,2,3,4-tetrahydroquinoxalin-6-yl)benzoyl)piperazine-1-carboxylate (0.2 M in 1,2-dichloroethane, 100 μL, 0.02 mmol), N,N-diisopropylethyl amine (25 μL, 0.14 mmol), and phenyl chloroformate (6.23 mg, 0.04 mmol), and the mixture was shaken at 50° C. for 2 h. Methanol (50 μL) was added and the mixture was shaken at 50° C. for 10 min. HCl (4 M in dioxane, 0.075 mL, 0.30 mmol) was added and the reaction was shaken at 50° C. for 2 h. The mixture was concentrated and the residue was purified by mass triggered preparatory HPLC. The product-containing fractions were combined and concentrated in a Genevac to afford phenyl (S)-4-acetyl-3-methyl-7-(4-(piperazine-1-carbonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-carboxylate. MS (ESI, pos. ion) m/z 499.

Workup

  1. customA reaction
  2. stirringthe mixture was shaken at 50° C. for 10 min
  3. stirringthe reaction was shaken at 50° C. for 2 h
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by mass
  6. concentrationconcentrated in a Genevac

Sources & evidence

ORD record
ord-46bfc13ca8bc41cebaad845fbbef9254
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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