Triethylamine → HCID 86668284, compound

HRID 2167632Notes

Reaction equation

HRID 2167632 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:16][CH:15]=[CH:14][CH:13]=2.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 18783942tert-Butyl (4-((3-aminoquinolin-4-yl)amino)butyl)carbamate

Product 1

HCID 86668284HCID 86668284, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (iii) (10.38 g) was added dropwise to a solution of the product from step (ii) (28 g) at 0° C. in DCM (400 mL) and triethylamine (11.81 mL) over 1 hour then heated under reflux overnight. The reaction was cooled to rt and the solution washed with saturated sodium hydrogen carbonate, dried and solvent removed. The crude product was purified on silica to give the subtitle compound as a solid (26 g); MS multimode (+) 399.

Workup

  1. temperatureunder reflux overnight
  2. washthe solution washed with saturated sodium hydrogen carbonate
  3. customdried
  4. customsolvent removed
  5. customThe crude product was purified on silica

Sources & evidence

ORD record
ord-26da249056a24f25815142a2278bc8d3
Source dataset
uspto-grants-2015_06
Patent number
US09045472B2

Reaction notes

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