Chloroform → HCID 10015239, compound

HRID 1373897Notes

Reaction equation

HRID 1373897 reaction equation
[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:19])([CH3:3])[CH3:2].[NH4+:20].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(Cl)(Cl)Cl>C(Cl)Cl.O>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:20])[C:8]=2[N:7]=[C:6]1[CH3:19])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 21075808HCID 21075808, compound

Product 1

HCID 10015239HCID 10015239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-isopropyl(2-methyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.95 g, 7.61 mmol) in 75 mL of CH2Cl2 was treated with 35 mL of concentrated NH4OH solution. To the rapidly stirred solution was added p-toluenesulfonyl chloride (1.52 g, 7.99 mmol). After stirring for 30 min, the reaction mixture was treated with CHCl3 (25 mL) and H2O (35 mL). The layers were separated and the organic portion was washed with 2% Na2CO3 solution (2×), H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give a light-yellow solid. Crystallization from propyl acetate gave N1-isopropyl-2-methyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (747 mg) as off-white crystals. mp 227–229° C.; 1H NMR (300 MHz, CDCl3) δ 8.19 (dd, J=8.2, 1.1 Hz, 1H), 7.79 (dd, J=8.4, 0.7 Hz, 1H), 7.53–7.45 (m, 1H), 7.33–7.26 (m, 1H), 5.42 (s, 2H), 4.91 (d, J=1.4 Hz, 1H), 3.73–3.62 (m, 1H), 2.64 (s, 3H), 1.15 (d, J=6.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 151.4, 151.3, 144.9, 133.3, 127.6, 127.3, 124.6, 122.4, 120.2, 115.4, 52.3, 20.9, 13.8; MS m/z 256 (M+H)+; Anal. Calcd for C14H17N5: C, 65.86; H, 6.71; N, 27.43; Found: C, 65.59; H, 6.56; N, 27.09.

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed with 2% Na2CO3 solution (2×), H2O and brine
  3. dry with materialThe organic portion was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light-yellow solid
  7. customCrystallization from propyl acetate

Sources & evidence

ORD record
ord-03c5a564147a49ae9fcfbb7241320cda
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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