Sulfuric acid magnesium salt (1:1) → N1-[5-(1H imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide

HRID 353821Notes

Reaction equation

HRID 353821 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.S([O-])([O-])(=O)=O.[Mg+2].[CH2:35](OC(OCC)OCC)C>[Pt].C1(C)C=CC=CC=1>[N:14]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:1]=[CH:35]1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 31214Ethyl orthoformateHCID 23512735N-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide

Product 1

HCID 23512691N1-[5-(1H imidazo[4,5-c]quinolin-1-yl)pentyl]benzamideYield 71.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

A catalytic amount of platinum on carbon was added to a suspension of N1-{5-[(3-nitroquinolin-4-yl)amino]pentyl}benzamide (5 g, 13.2 mmol) in toluene (250 mL). The reaction mixture was placed under a hydrogen atmosphere at 50 psi (3.4×104 pascals) on a Parr apparatus. After about 2 hours an oily ball had formed in the bottom of the Parr bottle. Magnesium sulfate and additional catalyst were added and the hydrogenation was continued overnight. The reaction mixture was filtered to remove the catalyst. The residue in the Parr bottle was combined with isopropyl alcohol (150 mL), heated on a steam bath and then filtered. HPLC analysis indicated that both filtrates contained product so they were combined and concentrated under vacuum to provide crude N1-{5-[(3-aminoquinolin-4-yl)amino]pentyl}benzamide. This material was combined with toluene (250 mL). Triethylorthoformate (4 g, 26.4 mmol) was added and the reaction mixture was heated at reflux with a Vigreux column for 2 hours. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration to provide 3.4 g of N1-[5-(1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide as a solid, m.p. 171.5-172.5° C. 1H NMR (500 MHz, DMSO-d6) δ 9.22 (s, 1H), 8.43 (t, J=6.0 Hz, 2H), 8.38 (m, 1H), 8.18 (m, 1H), 7.80 (d, J=7.0 Hz, 2H), 7.73 (m, 2H), 7.51 (t, J=7.0 Hz, 1H), 7.45 (t, J=7.0 Hz, 2H), 4.72 (t, J=7.5 Hz, 2H), 3.25 (q, J=6.0 Hz, 2H), 1.94 (quintet, J=7.5 Hz, 2H), 1.58 (quintet, J=7.5 Hz, 2H), 1.40 (quintet, J=8.5 Hz, 2H).

Workup

  1. customAfter about 2 hours an oily ball had formed in the bottom of the Parr bottle
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. temperatureheated on a steam bath
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto provide crude N1-{5-[(3-aminoquinolin-4-yl)amino]pentyl}benzamide
  8. temperaturethe reaction mixture was heated
  9. temperatureat reflux with a Vigreux column for 2 hours
  10. customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-7355af6719a341e8a031fd901ef0d5af
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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