Chloroform → HCID 10000600, compound

HRID 1373935Notes

Reaction equation

HRID 1373935 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[C:7]1[CH2:20][O:21][CH2:22][CH3:23].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(Cl)(Cl)Cl>C(Cl)Cl.CO>[NH2:19][C:10]1[C:9]2[N:8]=[C:7]([CH2:20][O:21][CH2:22][CH3:23])[N:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][S:32]([CH3:31])(=[O:34])=[O:33])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86594228HCID 86594228, compound

Product 1

HCID 10000600HCID 10000600, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N1-(3-aminopropyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.250 g, 0.795 mmol) in 10 mL of CH2Cl2 was treated with triethylamine (0.221 mL, 1.67 mmol) under an atmosphere of nitrogen and cooled to 0° C. The reaction mixture was treated dropwise with methanesulfonyl chloride (0.065 mL, 0.835 mmol). After 16 h, the reaction mixture was quenched by 10% Na2CO3 solution, diluted with CHCl3 and the phases were separated. The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a light yellow solid. Chromatography (SiO2, 95:5 CHCl3:MeOH) gave an off-white foam. The foam was triturated with diethyl ether and filtered to give N-{3-[(4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)amino]propyl}methanesulfonamide (0.164 g) as an off white solid. mp 148–150° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.46 (d, J=7.8 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.44 (t, J=7.1 Hz, 1H), 7.25 (t, J=7.4 Hz, 1H), 7.05–6.95 (m, 2H), 6.61 (s, 2H), 4.76 (s, 2H), 3.62 (q, J=7.0 Hz, 2H), 3.22 (q, J=6.8 Hz, 2H), 3.07 (q, J=6.2 Hz, 2H), 2.88 (s, 3H), 1.78 (p, J=6.3 Hz, 2H), 1.18 (t, J=7.0 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 152.3, 149.5, 145.3, 132.5, 127.4, 126.1, 124.2, 121.3, 121.3, 114.7, 65.9, 63.1, 49.9, 39.6, 28.1, 15.4; MS (APCI) m/z 393 (M+H)+; Anal. Calcd for C17H24N6O3: C, 52.03; H, 6.16; N, 21.41; Found: C, 51.84; H, 6.28; N, 21.18.

Workup

  1. customthe reaction mixture was quenched by 10% Na2CO3 solution
  2. additiondiluted with CHCl3
  3. customthe phases were separated
  4. washThe organic portion was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a light yellow solid
  9. customThe foam was triturated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ee63f9a65976427c9dc99cb61e6ef78c
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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