Water → HCID 10108777, compound

HRID 1373906Notes

Reaction equation

HRID 1373906 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:18]=1)[CH3:2].[NH4+:23].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:23])[C:8]=2[N:18]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 69197839HCID 69197839, compound

Product 1

HCID 10108777HCID 10108777, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

A solution of N-(2-ethoxymethy-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)isopropylamine (0.93 g, 3.10 mmol) in 25 mL of CH2Cl2 was treated with 15 mL of concentrated NH4OH solution. To the rapidly stirred solution was added p-toluenesulfonyl chloride (620 mg, 3.25 mmol). After stirring for 30 min, the reaction was treated with CH2Cl2 (20 mL) and H2O (15 mL). The layers were separated and the organic portion was washed with 2% Na2CO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give a tan solid. Chromatography (SiO2, 5% MeOH/CHCl3) gave 2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (368 mg) as a tan solid. mp 162–164° C.; 1H NMR (300 MHz, CDCl3) δ 8.60 (dd, J=8.2, 1.1 Hz, 1H), 7.77 (dd, J=8.4, 0.7 Hz, 1H), 7.54–7.47 (m, 1H), 7.33–7.54 (m, 1H), 5.55 (d, J=3.2 Hz, 1H), 5.41 (s, 2H), 4.89 (s, 2H), 3.73–3.60 (m, 3H), 1.26 (t, J=7.0 Hz, 3H); 1.15 (d, J=6.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 151.1, 148.7, 145.0, 127.7, 126.6, 123.9, 121.9, 121.3, 115.4, 66.8, 65.7, 52.5, 20.6, 15.1; MS m/z 300 (M+H)+; Anal. Calcd for C16H21N5O.0.48 H2O: C, 62.39; H, 7.19; N, 22.74; Found: C, 62.38, H, 6.90; N, 22.79.

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed with 2% Na2CO3 solution, H2O and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a tan solid

Sources & evidence

ORD record
ord-8589f8ab2892468a969986b9352530e0
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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