Morpholine → HCID 69506694, compound

HRID 2366617Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)[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:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:25])[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

Reactant 3

HCID 8083Morpholine2×

HCID 65578Oxalyl chloride2×

HCID 69506708HCID 69506708, compound

Product 1

HCID 69506694HCID 69506694, compoundYield 92.4%

Procedure

6-[2-(2-Methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]hexanoic acid (4.1 g, 12 mmol) was treated with oxalyl chloride (1.89 mL, 21.6 mmol) and morpholine (3.15 mL, 36.0 mmol) according to a modification of the method described in Part F of Example 6. The reaction with oxalyl chloride was carried out at ambient temperature, and the reaction with morpholine was complete after two hours. Following the work-up procedure, 4.55 g of 2-(2-methoxyethyl)-1-(6-morpholin-4-yl-6-oxohexyl)-1H-imidazo[4,5-c]quinoline were obtained.

Workup

customwas carried out at ambient temperature

Sources & evidence

ORD record: ord-ff9d60871ac245f4a3e2c92bac30917b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697873B2

Reaction notes

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