Triethylamine → HCID 11640961, compound

HRID 1373971Notes

Reaction equation

HRID 1373971 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:19]([NH:20][CH:21]([CH3:23])[CH3:22])[C:18]([CH2:24][O:25][CH2:26][CH3:27])=[N:17][C:11]=3[C:12]([NH2:16])=[N:13][C:14]=2[CH:15]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl.C(Cl)(Cl)Cl>[NH2:16][C:12]1[C:11]2[N:17]=[C:18]([CH2:24][O:25][CH2:26][CH3:27])[N:19]([NH:20][CH:21]([CH3:22])[CH3:23])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:15][C:14]=2[N:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69435139HCID 69435139, compound

Product 1

HCID 11640961HCID 11640961, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(3-aminopropoxy)-2-ethoxymethyl-N1-isopropyl-1H-imidazo[4,5-c]quinoline-1,4-diamine (0.84 g, 2.26 mmol) in 25 mL of CH2Cl2 was placed under an atmosphere of nitrogen. The solution was treated with triethylamine (0.63 mL, 4.75 mmol) and cooled in an ice water bath. The solution was slowly treated with methanesulfonyl chloride (0.184 mL, 2.37). The reaction was stirred and allowed to slowly come to ambient temperature. After 16 h, the reaction mixture was diluted with CHCl3 (20 mL) and transferred to a separatory funnel. The organic solution was washed with 10% Na2CO3 solution (15 mL), H2O (15 mL) and brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan foam. The foam was purified by chromatography (SiO2, 10–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3) to give a light yellow solid. The solid was crystallized from MeCN to yield N-(3-{[4-amino-2-(ethoxymethyl)-1-(isopropylamino)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propyl)methanesulfonamide (0.295 g) as white crystals. mp 181–183° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.46 (d, J=9.0 Hz, 1H), 7.09 (t, J=6.8 Hz, 1H), 7.02 (d, J=2.6 Hz, 1H), 6.90 (d, J=2.1 Hz, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.54 (s, 2H), 4.71 (s, 2H), 4.11 (t, J=6.1 Hz, 2H), 3.64–3.58 (m, 3H), 3.14 (q, J=6.1 Hz, 2H), 2.91 (s, 3H), 1.96 (p, J=6.6 Hz, 2H), 1.15 (t, J=7.0 Hz, 3H), 1.01 (d, J=6.1 Hz, 6H); 13C NMR (75 MHz, DMSO-d6) δ 158.1, 152.6, 149.4, 147.2, 133.7, 122.6, 111.5, 109.1, 107.9, 65.8, 65.0, 63.0, 51.6, 29.7, 20.6, 15.3; MS (APCI) m/z 451 (M+H)+; Anal. Calcd for C20H30N6O4S: C, 53.32; H, 6.71; N, 18.65; S, 7.12; Found: C, 53.44; H, 6.68; N, 18.83; S, 7.09.

Workup

  1. temperaturecooled in an ice water bath
  2. customto slowly come to ambient temperature
  3. customtransferred to a separatory funnel
  4. washThe organic solution was washed with 10% Na2CO3 solution (15 mL), H2O (15 mL) and brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a tan foam
  9. customThe foam was purified by chromatography (SiO2, 10–50% (80:18:2 CHCl3:MeOH:NH4OH) in CHCl3)
  10. customto give a light yellow solid
  11. customThe solid was crystallized from MeCN

Sources & evidence

ORD record
ord-f4a1c817a49d49909ddfa11a444c9523
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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