Triethylamine → HCID 69506730, compound

HRID 2366667Notes

Reaction equation

HRID 2366667 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:22]([O:24][CH2:25][C:26](Cl)=O)[CH3:23].C(N(CC)CC)C>C(O)C>[CH2:22]([O:24][CH2:25][C:26]1[N:12]([CH2:13][C:14]([CH3:20])([CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:23]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 84189Ethoxyacetyl chloride2×HCID 57447056HCID 57447056, compound

Product 1

HCID 69506730HCID 69506730, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A modification of the method described in Part C of Example 5 was used to treat ethyl 3-[(3-aminoquinolin-4-yl)amino]-2,2-dimethylpropanoate (15.5 g, 60.2 mmol, prepared in Parts A through D of Example 26) with ethoxyacetyl chloride (8.7 g, 71 mmol) followed by triethylamine (24.4 mL, 175 mmol). The reaction with ethoxyacetyl chloride was stirred overnight, and the reaction with triethylamine was heated at reflux in ethanol (125 mL) for four days. Following the work-up procedure, the crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 100:0 to 95:5) to provide 7.9 g of ethyl 3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropanoate as an oil.

Workup

  1. temperaturewas heated
  2. customthe crude product was purified by column chromatography on silica gel (
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-21427562f4514c5c985c0024340f59de
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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