Water → HCID 21936609, compound

HRID 1793158Notes

Reaction equation

HRID 1793158 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[C:33](Cl)(=[O:36])[CH2:34][CH3:35].O>C(Cl)Cl>[C:33]([NH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:36])[CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 12106200Tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy)ethylcarbamate

Product 1

HCID 21936609HCID 21936609, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (32.0 g, 92.0 mmol) in 300 mL of CH2Cl2 was treated with triethylamine (19.2 mL, 138.0 mmol). The reaction was chilled in an ice water bath and then propionyl chloride (9.40 mL, 108.2 mmol) was added dropwise. After stirring for 18 h, the reaction was treated with water (150 mL) and the layers were separated. The aqueous portion was extracted with CH2Cl2 (3×50 mL). The combined organic portions were washed with 1% Na2CO3, water, brine, dried over Na2SO4, filtered and concentrated to yield a red sticky solid. The solid was triturated with ether and filtered to yield 16.5 g of tert-butyl 2-(2-{[3-(propionylamino)quinolin-4-yl]amino}ethoxy)ethylcarbamate as an off white powder.

Workup

  1. temperatureThe reaction was chilled in an ice water bath
  2. customthe layers were separated
  3. extractionThe aqueous portion was extracted with CH2Cl2 (3×50 mL)
  4. washThe combined organic portions were washed with 1% Na2CO3, water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a red sticky solid
  9. customThe solid was triturated with ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-0569a42b9c0347a4bad5f00be9b86b7b
Source dataset
uspto-grants-2006_07
Patent number
US07078523B2

Reaction notes

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