4-Toluenesulfonyl chloride → HCID 10336572, compound

HRID 1373924Notes

Reaction equation

HRID 1373924 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[NH4+:35].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl.C(Cl)(Cl)Cl.O.CO>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:35])[C:8]=2[N:17]=1)[CH3:2]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21075788HCID 21075788, compound

Product 1

HCID 10336572HCID 10336572, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(3-methylbutyl)amine (1.24 g, 3.97 mmol) in 45 mL of CH2Cl2 was treated with MCPBA (1.87 g, 7.04 mmol, 77% max). After 1.5 h, the reaction mixture was treated with 15 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (0.795 g, 4.17 mmol). After 30 min, the reaction mixture was diluted with CHCl3 and water and the phases were separated. The organic portion was washed with 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a sticky orange foam. Chromatography (SiO2, 97:3 CHCl3:MeOH) gave an off white foam. The foam was triturated with diethyl ether and hexanes and filtered to give 2-ethoxymethyl-N1-(3-methylbutyl)-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.435 g) as a cream colored solid. mp 129–132° C.; 1H NMR (300 MHz, CDCl3) δ 8.48 (dd, J=8.1, 1.1 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 7.56–7.50 (m, 1H), 7.36–7.30 (m, 1H), 5.59 (t, J=6.7 Hz, 1H), 5.42 (s, 2H), 4.87 (s, 2H), 3.64 (q, J=7.0 Hz, 2H), 3.29 (q, J=7.0 Hz, 2H), 1.76 (s, J=6.7 Hz, 1H), 1.60 (q, J=6.9 Hz, 2H), 1.27 (t, J=7.0 Hz, 3H), 0.97 (d, J=6.6 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 151.2, 147.8, 144.9, 133.1, 127.8, 126.6, 124.0, 122.3, 120.7, 115.2, 66.8, 65.3, 51.1, 36.7, 26.0, 22.6, 15.1; MS (APCI) m/z 328 (M+H)+; Anal. Calcd for C18H25N5O.0.06H2O: C, 65.81; H, 7.71; N, 21.32; Found: C, 65.42; H, 7.75; N, 21.11. Karl Fischer analysis 0.32% water.

Workup

  1. waitAfter 30 min
  2. customthe phases were separated
  3. washThe organic portion was washed with 5% Na2CO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a sticky orange foam
  8. customThe foam was triturated with diethyl ether and hexanes
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c85205dbaf514996a74cfc09794b03be
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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