Triethylamine → HCID 58833652, compound

HRID 2203507Notes

Reaction equation

HRID 2203507 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:28]([CH2:34][CH2:35][CH3:36])=[N:27][C:21]=3[C:22]([NH2:26])=[N:23][C:24]=2[CH:25]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:26][C:22]1[C:21]2[N:27]=[C:28]([CH2:34][CH2:35][CH3:36])[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][NH:11][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)=[CH:25][C:24]=2[N:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 588337127-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 58833652HCID 58833652, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Nicotinoyl chloride hydrochloride (0.23 g, 1.29 mmol) was added in one portion to a solution of 7-(3-aminopropoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.460 g, 1.29 mmol) and triethylamine (0.383 mL, 2.75 mmol) in chloroform (15 mL), and the reaction was stirred for 16 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate and stirred for 30 minutes. The aqueous layer was separated and extracted with chloroform. The combined organic fractions were washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting pale yellow oil was triturated with acetonitrile, which was removed under reduced pressure. The resulting solid was recrystallized from acetonitrile to yield 0.310 g of N-{3-[4-amino-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yloxy]propyl}nicotinamide as off-white, granular crystals, mp 172-174° C.

Workup

  1. stirringstirred for 30 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted with chloroform
  4. washThe combined organic fractions were washed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting pale yellow oil was triturated with acetonitrile, which
  9. customwas removed under reduced pressure
  10. customThe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-45c75f099f07446bbdaec0c7012e1d60
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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