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

HRID 2366683Notes

Reaction equation

HRID 2366683 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C(Cl)(=O)C(Cl)=O.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[N:30]1([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][N:5]2[C:6]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[CH:8][C:7]=3[N:16]=[C:4]2[CH2:1][CH2:2][CH3:3])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 8083Morpholine2×HCID 65578Oxalyl chloride2×HCID 574470705-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid

Product 1

HCID 695067201-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolineYield 98.8%

Procedure

A modification of the method described in Part F of Example 6 was used to treat 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoic acid (5.14 g, 16.5 mmol) with oxalyl chloride (2.59 mL, 29.7 mmol) and morpholine (4.33 mL, 49.5 mmol). The oxalyl chloride addition was carried out at ambient temperature, and the reaction with morpholine was complete in three hours. Following the work-up procedure, 6.2 g of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinoline were obtained.

Workup

  1. customwas carried out at ambient temperature

Sources & evidence

ORD record
ord-63aafa9d1ab84116925eccc58bdf3dac
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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