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

HRID 746517Notes

Reaction equation

HRID 746517 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-edd561d65cff4a8e84f79fcf99f9db60
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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