4-Toluenesulfonyl chloride → tert-butyl 6-amino-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364031Notes

Reaction equation

HRID 1364031 reaction equation
[OH-].[NH4+:2].[O-][N+:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2[N:14]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C:15]3=[N:16][C:6]=2[CH:5]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[NH2:2][C:5]1[C:6]2[N:16]=[C:15]3[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20][N:14]3[C:7]=2[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66958567tert-butyl 5-oxido-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Product 1

HCID 58923896tert-butyl 6-amino-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Concentrated ammonium hydroxide (160 mL) was added with vigorous stirring to a solution of tert-butyl 5-oxido-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (28.49 g, 83.7 mmol) in dichloromethane (300 mL). p-Toluenesulfonyl chloride (15.96 g, 83.7 mmol) was added in small portions over a period of five minutes, after which an analysis by HPLC indicated that the reaction was complete. The aqueous layer was then extracted with dichloromethane (3×150 mL), and the combined organic fractions were washed with 1% aqueous sodium carbonate (2×150 mL). The combined aqueous washings were extracted with dichloromethane (200 mL), and all organic fractions were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide tert-butyl 6-amino-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate as a yellow solid.

Workup

  1. extractionThe aqueous layer was then extracted with dichloromethane (3×150 mL)
  2. washthe combined organic fractions were washed with 1% aqueous sodium carbonate (2×150 mL)
  3. extractionThe combined aqueous washings were extracted with dichloromethane (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f62b04918df414db3644007284021c6
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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