Pyrrolidine → (S)-1-(2-methyl-6-(4-(methylsulfonyl)phenyl)-4-(pyrrolidine-1-carbonyl)-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

HRID 1485755Notes

Reaction equation

HRID 1485755 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH:14]([N:17]([CH2:21][CH3:22])[CH:18]([CH3:20])C)(C)C.[CH3:23][C@H:24]1[CH2:33][NH:32][C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:34]3[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=3)[CH:30]=2)[N:25]1[C:44](=[O:46])[CH3:45].N1CCCC1>>[CH3:23][C@H:24]1[CH2:33][N:32]([C:14]([N:17]2[CH2:18][CH2:20][CH2:22][CH2:21]2)=[O:3])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:34]3[CH:35]=[CH:36][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:38][CH:39]=3)[CH:30]=2)[N:25]1[C:44](=[O:46])[CH3:45]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 118078872HCID 118078872, compound

Product 1

HCID 118079327(S)-1-(2-methyl-6-(4-(methylsulfonyl)phenyl)-4-(pyrrolidine-1-carbonyl)-3,4-dihydroquinoxalin-1(2H)-yl)ethanoneYield 43%

Conditions

Temperature
50 °C

Procedure

4-Nitrophenyl chloroformate (0.4 M in 1,4-dioxane, 0.075 mL, 0.030 mmol) and N,N-diisopropylethylamine (0.015 mL, 0.086 mmol) were added to (S)-1-(2-methyl-6-(4-(methylsulfonyl)phenyl)-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.2 M in 1,4-dioxane, 0.100 mL, 0.020 mmol) and the mixture stirred at 50° C. for 1 h. Pyrrolidine (0.2 M in 1,4-dioxane, 0.200 mL, 0.040 mmol) was then added and the mixture was stirred at 80° C. for 16 h. The reaction was concentrated and the crude product was purified by mass-triggered preparatory HPLC. The product-containing fractions were combined and concentrated to afford (S)-1-(2-methyl-6-(4-(methylsulfonyl)phenyl)-4-(pyrrolidine-1-carbonyl)-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.0038 g, 43% yield). MS (ESI, pos. ion) m/z 442

Workup

  1. stirringthe mixture was stirred at 80° C. for 16 h
  2. concentrationThe reaction was concentrated
  3. customthe crude product was purified by mass-triggered preparatory HPLC
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8cf8c2fb4fb2459493d029ca0d40cbb5
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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