Triethylamine → HCID 10409430, compound

HRID 1837585Notes

Reaction equation

HRID 1837585 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:25])[C:15]=2[N:14]=[C:13]1[CH2:26][CH2:27][O:28][CH3:29].[N:30]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:25][C:16]1[C:15]2[N:14]=[C:13]([CH2:26][CH2:27][O:28][CH3:29])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:36]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:37])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 848104-Morpholinecarbonyl chlorideHCID 223444281-(3-aminopropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 10409430HCID 10409430, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (1.04 mL, 7.51 mmol) was added to a chilled (0°) solution of 1-(3-aminopropyl)-2-(2-methoxyethyl)1H-imidazo[4,5-c]quinolin-4-amine (1.50 g, 5.01 mmol) in chloroform (75 mL). 4-Morpholinecarbonyl chloride (830 mg, 5.51 mmol) was added dropwise. The reaction was allowed to warm to ambient temperature and was maintained over the weekend. An equal volume of aqueous 1% sodium carbonate was added with vigorous stirring. A precipitate was isolated by filtration to provide 1.73 g of crude product as a white powder. This material was purified by column chromatography (silica gel eluting with a 0-5% methanol in chloroform gradient) and then triturated with diethyl ether to provide 1.6 g of N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide as a white powder, m.p. 194.0-196.0° C. Analysis: Calculated for C21H28N6O3: %C, 61.15; %H, 6.84; %N, 20.37; Found: %C, 60.82; %H, 6.94; %N, 20.34.

Workup

  1. temperaturewas maintained over the weekend
  2. customA precipitate was isolated by filtration
  3. customto provide 1.73 g of crude product as a white powder
  4. customThis material was purified by column chromatography (silica gel eluting with a 0-5% methanol in chloroform gradient) and
  5. customthen triturated with diethyl ether

Sources & evidence

ORD record
ord-ee015596bfdc4c12bdc96f1a61898232
Source dataset
uspto-grants-2004_08
Patent number
US06784188B2

Reaction notes

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