4-Morpholinecarbonyl chloride → HCID 22478987, compound

HRID 1368155Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:18])[C:8]=2[N:7]=[C:6]1[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[N:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[NH2:18][C:9]1[C:8]2[N:7]=[C:6]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:35]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:36])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

Reactant 2

HCID 848104-Morpholinecarbonyl chloride

HCID 22344439HCID 22344439, compound

Product 1

HCID 22478987HCID 22478987, compoundYield 69.3%

Procedure

Using the general method of Example 150, 1-(3-aminopropyl)-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 5.32 mmol) was reacted with 4-morpholinecarbonyl chloride (880 mg, 5.86 mmol) to provide 1.8 g of N-{3-[4-amino-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide as a light yellow crystalline solid, m.p. 198.8-199.9° C. Analysis: Calculated for C27H32N6O3%C, 66.37; %H, 6.60; %N, 17.20; Found: %C, 66.31; %H, 6.70; %N, 17.40.

Sources & evidence

ORD record: ord-907f0fcea8d2478a80062632578380e5
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573273B1

Reaction notes

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