Benzoyl chloride → N1-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]benzamide

HRID 353833Notes

Reaction equation

HRID 353833 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[NH2:17][C:8]1[C:7]2[N:6]=[CH:5][N:4]([CH2:3][CH2:2][NH:1][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 235127191-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 9862386N1-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]benzamideYield 25.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(2-aminoethyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.40 g, 1.76 mmol) and anhydrous pyridine (60 mL) was heated until a clear solution was obtained. The solution was then cooled with an ice bath. Benzoyl chloride (0.25 g, 1.76 mmol) was added. The reaction mixture was maintained at ambient temperature overnight and then concentrated under vacuum. The residue was slurried with water (200 mL) and a solid was isolated by filtration. This material was recrystallized from isopropyl alcohol to provide 0.15 g of N1-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]benzamide as a white powder, m.p. 295° C. 1H NMR (500 MHz, DMSO-d6) δ 8.50 (t, J=6.0 Hz, 1H), 8.23 (d, J=8.0 Hz, 1H), 8.04 (s, 1H), 7.75(d, J=8.0 Hz, 2H), 7.64 (d, J=8.0 Hz, 1H), 7.49 (t, J=8.0 Hz, 1H), 7.43 (t, J=8.0, 1H), 7.41 (t, J=8.0 Hz, 2H), 7.25 (t, J=8.0 Hz, 1H), 6.28 (broad s, 2H), 4.80(t, J=7.0 Hz, 2H), 3.80(q, J=6.0 Hz, 2H); MS (EI) m/e 331.1429 (331.1433 calcd for C19H17N5O).

Workup

  1. temperaturewas heated until a clear solution
  2. customwas obtained
  3. temperatureThe solution was then cooled with an ice bath
  4. concentrationconcentrated under vacuum
  5. customa solid was isolated by filtration
  6. customThis material was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-0b0e33a7b88049dfa8e1179d8f33736a
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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