Triethylamine → ethyl 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoate

HRID 2366687Notes

Reaction equation

HRID 2366687 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][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:22][O:23][CH2:24][CH2:25][C:26](Cl)=O.C(N(CC)CC)C>>[CH3:22][O:23][CH2:24][CH2:25][C:26]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[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

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27597283-Methoxypropanoyl chlorideHCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate

Product 1

HCID 69506690ethyl 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoateYield 90.8%

Procedure

Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate (23.0 g, 88.6 mmol, prepared in Parts A and B of Example 34) was treated according to the method described in Part A of Example 12. The addition of methoxypropionyl chloride (12.97 g, 106.3 mmol) was carried out at 0° C., and the reaction was stirred at ambient temperature for two hours. The reaction with triethylamine (49.4 g, 354 mmol) was heated at reflux for four hours. After the work-up procedure, 28.6 g of ethyl 5-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoate were obtained as a brown oil.

Workup

  1. customwas carried out at 0° C.
  2. temperaturewas heated
  3. temperatureat reflux for four hours

Sources & evidence

ORD record
ord-adeb139b8e9a4513aeab418f99c82dc4
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…