Morpholine → 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline

HRID 2366689Notes

Reaction equation

HRID 2366689 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1.C(Cl)(=O)C(Cl)=O.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 695067285-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoic acid

Product 1

HCID 695066852-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinolineYield 96.4%

Procedure

5-[2-(2-Methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanoic acid (5.5 g, 17 mmol) was treated according to a modification of the method described in Part F of Example 6. The reaction with oxalyl chloride (2.63 mL, 30.2 mmol) was carried out at ambient temperature and was complete in 30 minutes. The reaction with morpholine (4.40 mL, 50.4 mmol) was complete after 30 minutes. Following the work-up procedure, 6.5 g of 2-(2-methoxyethyl)-1-(5-morpholin-4-yl-5-oxopentyl)-1H-imidazo[4,5-c]quinoline were obtained.

Workup

  1. customwas carried out at ambient temperature
  2. waitwas complete after 30 minutes

Sources & evidence

ORD record
ord-9fd1809e6efc468593fcfa0f0f6098e3
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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