Water → HCID 9997831, compound

HRID 1373903Notes

Reaction equation

HRID 1373903 reaction equation
[CH2:1]([NH:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:14]([O-])=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:23][O:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:27].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[CH2:1]([NH:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:27])[C:12]=2[N:11]=[C:10]1[CH2:23][O:24][CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 69203575HCID 69203575, compound

Product 1

HCID 9997831HCID 9997831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-benzyl-(2-ethoxymethy-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (0.99 g, 2.84 mmol) in 50 mL of CH2Cl2 was treated with 25 mL of concentrated NH4OH solution. To the rapidly stirred solution was added p-toluenesulfonyl chloride (569 mg, 2.98 mmol). After stirring for 30 min, the reaction was treated with CH2Cl2 (50 mL) and H2O (25 mL). The layers were separated and the organic portion was washed 2% Na2CO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give a tan solid. Chromatography (SiO2, 2% MeOH/CHCl3 containing 0.5% concentrated NH4OH) followed by crystallization from propyl acetate gave N1-benzyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (148 mg) as white needles. mp 152–155° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.61 (dd, J=8.2, 1.2 Hz, 1H), 7.85–7.77 (m, 1H), 7.59–7.52 (m, 1H), 7.42–7.34 (m, 4H), 7.33–7.24 (m, 2H), 6.02 (t, J=6.6 Hz, 1H), 5.39 (s, 2H), 4.43 (s, 2H), 4.40 (d, J=6.7 Hz, 2H), 3.55 (q, J=7.0 Hz, 2H), 1.22 (t, J=7.0 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 151.1, 147.9, 144.9, 135.7, 129.2, 129.1, 128.6, 127.8, 126.7, 122.4, 120.7, 66.7, 65.3, 56.7, 15.0; MS m/z 348 (M+H)+; Anal. Calcd for C2OH21N5O.0.36H2O: C, 68.90; H, 6.11; N, 20.09; Found: C, 68.50; H, 6.07; N, 20.11.

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed 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
  7. customChromatography (SiO2, 2% MeOH/CHCl3 containing 0.5% concentrated NH4OH) followed by crystallization from propyl acetate

Sources & evidence

ORD record
ord-1c64ded461564f9a9dee6a83a27d42f6
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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