Triethylamine → HCID 86619537, compound

HRID 1803385Notes

Reaction equation

HRID 1803385 reaction equation
[NH2:1][C@H:2]([CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.Cl[C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[CH:30][C:29]=1[N+:38]([O-:40])=[O:39]>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[CH3:19][S:16]([NH:15][CH2:14][C@@H:2]([NH:1][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[CH:30][C:29]=1[N+:38]([O-:40])=[O:39])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])(=[O:18])=[O:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 86619538HCID 86619538, compound

Product 1

HCID 86619537HCID 86619537, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (4S)-4-amino-5-[(methylsulfonyl)amino]pentylcarbamate (6.88 g, 23.3 mmol) was dissolved in 100 mL of dry CH2Cl2 and the solution was cooled to 0° C. under N2. Triethylamine (6.49 mL, 46.6 mmol) and 4-chloro-3-nitroquinoline (4.85 g, 23.3 mmol) were then added and the reaction was allowed to warm to ambient temperature and stirred for 2 days. The reaction mixture was then concentrated under reduced pressure to give a yellow solid. The solid was triturated with 100 mL of hot H2O with stirring. The suspension was cooled and filtered to give 12.0 g of a pasty, yellow solid. The pasty solid was dissolved in methanol and CHCl3 and concentrated to give a yellow solid. The solid was then stirred in 100 mL of hot CHCl3, cooled and the solid was collected by filtration to give tert-butyl (4S)-5-[(methylsulfonyl)amino]-4-[(3-nitroquinolin-4-yl)amino]pentylcarbamate (8.00 g) as a yellow powder.

Workup

  1. temperatureto warm to ambient temperature
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customto give a yellow solid
  4. customThe solid was triturated with 100 mL of hot H2O
  5. stirringwith stirring
  6. temperatureThe suspension was cooled
  7. filtrationfiltered
  8. customto give 12.0 g of a pasty, yellow solid
  9. concentrationCHCl3 and concentrated
  10. customto give a yellow solid
  11. temperaturecooled
  12. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-6e862c0a47284b6ab78ea2922e514897
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

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