Triethylamine → HCID 21984045, compound

HRID 9512Notes

Reaction equation

HRID 9512 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-dc51e2ec186444cea2088f7c0632f2df
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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