Triethylamine → HCID 21984045, compound

HRID 1818258Notes

Reaction equation

HRID 1818258 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[C:26]2[C:25]3[CH:24]=[CH:23][C:22]([Br:27])=[CH:21][C:20]=3[N:19]=[C:18]([NH2:28])[C:17]=2[N:16]=[C:15]1[CH2:29][O:30][CH2:31][CH3:32].C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:28][C:18]1[C:17]2[N:16]=[C:15]([CH2:29][O:30][CH2:31][CH3:32])[N:14]([CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[C:26]=2[C:25]2[CH:24]=[CH:23][C:22]([Br:27])=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chloride2×HCID 219841661-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 21984045HCID 21984045, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cyclopentanecarbonyl chloride (0.80 mL, 6.6 mmol) was added dropwise over a period of five minutes to a suspension of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) and triethylamine (0.78 mL, 5.6 mmol) in chloroform (200 mL). The reaction was stirred for 2.5 hours and then stored for three days in a refrigerator. Additional cyclopentanecarbonyl chloride (0.18 mL) was added, and the reaction was stirred for 30 minutes and treated as described for Examples 558-583. The crude product was recrystallized from isopropanol (13 mL/g), isolated by filtration, and dried overnight on the filter funnel to provide 1.60 g of N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}cyclopentanecarboxamide as a white solid.

Workup

  1. waitstored for three days in a refrigerator
  2. stirringthe reaction was stirred for 30 minutes
  3. additiontreated
  4. customThe crude product was recrystallized from isopropanol (13 mL/g)
  5. customisolated by filtration
  6. customdried overnight on the filter funnel

Sources & evidence

ORD record
ord-9e5c44acd4f64ffe93108a79e602e661
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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