Triethylamine → Tert-butyl 3-({2-[bis(4-methoxybenzyl)amino]-3-nitroquinolin-4-yl} amino)propylcarbamate

HRID 1097580Notes

Reaction equation

HRID 1097580 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.FC(F)(F)S(O[C:33]1[C:42]([N+:43]([O-:45])=[O:44])=[C:41]([NH:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1)(=O)=O>C1(C)C=CC=CC=1>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:26][CH:25]=2)[C:33]2[C:42]([N+:43]([O-:45])=[O:44])=[C:41]([NH:46][CH2:47][CH2:48][CH2:49][NH:50][C:51](=[O:52])[O:53][C:54]([CH3:56])([CH3:55])[CH3:57])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 866262904-({3-[(Tert-butoxycarbonyl)amino]propyl}amino)-3-nitroquinolin-2-yl trifluoromethanesulfonate

Product 1

HCID 66813901Tert-butyl 3-({2-[bis(4-methoxybenzyl)amino]-3-nitroquinolin-4-yl} amino)propylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (56.8 mL, 408 mmol) and N,N-bis(4-methoxybenzyl)amine (93.5 g, 0.340 mol) were sequentially added to a solution of 4-({3-[(tert-butoxycarbonyl)amino]propyl} amino)-3-nitroquinolin-2-yl trifluoromethanesulfonate (168 g, 0.340 mol) in toluene (200 mL) at ambient temperature. The solution was stirred at ambient temperature for a few minutes, heated at 65° C. overnight, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (>200 mL), and the resulting solution was washed three times with water, dried over magnesium sulfate, filtered through a layer of CELITE filter agent, concentrated under reduced pressure, and further dried under high vacuum to provide tert-butyl 3-({2-[bis(4-methoxybenzyl)amino]-3-nitroquinolin-4-yl} amino)propylcarbamate as a red oil, which was used without purification.

Workup

  1. temperatureheated at 65° C. overnight
  2. temperatureto cool to ambient temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (>200 mL)
  5. washthe resulting solution was washed three times with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered through a layer of CELITE filter agent
  8. concentrationconcentrated under reduced pressure
  9. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-05937f3c4def4ff38865fb52ecb33c0c
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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