4-Toluenesulfonyl chloride → HCID 10086951, compound

HRID 1373920Notes

Reaction equation

HRID 1373920 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][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]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[NH4+:34].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl.O.CO.C(Cl)(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH:20]([CH3:21])[CH3:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:34])[C:8]=2[N:17]=1)[CH3:2]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21075792HCID 21075792, compound

Product 1

HCID 10086951HCID 10086951, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isobutylamine (1.16 g, 3.89 mmol) in 30 mL of CH2Cl2 was treated with MCPBA (1.25 g, 5.05 mmol, 77% max). After 1.5 h, the reaction mixture was treated with 15 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (0.78 g, 4.08 mmol). After 30 min the reaction mixture was diluted with CH2Cl2 and water, and the phases were separated. The organic portion was washed with 2% Na2CO3 solution and water. The combined aqueous washes were back extracted with CHCl3 (2×). The combined organic portions were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a brown foam. Chromatography (SiO2, 97:3 CHCl3:MeOH) yielded 2-ethoxymethyl-N1-isobutyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.049 g) as an off white solid. mp 137–140° C.; 1H NMR (300 MHz, DMSO-d6, 350 K) δ 8.47 (dd, J=8.1, 0.9 Hz, 1H), 7.60 (d, J=8.3 Hz, 1H), 7.45–7.36 (m, 1H), 7.28–7.19 (m, 1H), 6.67 (t, J=6.2 Hz, 1H), 6.22 (s, 2H), 4.76 (s, 2H), 3.64 (q, J=7.0 Hz, 2H), 3.02 (t, J=6.4 Hz, 2H), 1.97 (s, J=6.7 Hz, 1H), 1.19 (t, J=7.0 Hz, 3H), 1.05 (d J=6.7 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 151.9, 148.9, 144.8, 131.9, 126.9, 125.7, 123.8, 120.8, 114.2, 65.4, 62.8, 59.6, 26.7, 20.5, 14.9; MS (APCI) m/z 314 (M+H)+; Anal. Calcd for C17H23N5O: C, 65.15; H, 7.40; N, 22.35; Found: C, 64.88; H, 7.39; N, 22.38.

Workup

  1. customthe phases were separated
  2. washThe organic portion was washed with 2% Na2CO3 solution and water
  3. extractionThe combined aqueous washes were back extracted with CHCl3 (2×)
  4. washThe combined organic portions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a brown foam

Sources & evidence

ORD record
ord-a731c918691442e5b84fe70928eb566d
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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