Hydrochloric Acid → HCID 57515406, compound

HRID 1363564Notes

Reaction equation

HRID 1363564 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[N:13]=[C:14]([CH2:37][O:38][CH2:39][CH3:40])[N:15]([CH2:16][C:17]3([O:30][CH2:31][CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:11]=2[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1>C(O)C>[CH2:39]([O:38][CH2:37][C:14]1[N:15]([CH2:16][C:17]2([O:30][CH2:31][CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[C:3]([NH2:2])[C:12]=2[N:13]=1)[CH3:40]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57515410HCID 57515410, compound

Product 1

HCID 57515406HCID 57515406, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of HCl in ethanol (4.2 M, 0.8 mL, 3.56 mmol) was added to a suspension of tert-butyl 4-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}-4-[2-(methylsulfonyl)ethoxy]piperidine-1-carboxylate (0.40 g, 0.71 mmol) in ethanol (4 mL) at rt. The resulting yellow solution was heated at reflux for 1.5 h. The reaction was stirred at rt for 16 h, then was concentrated under reduced pressure. The resulting solid was dissolved in water (20 mL) and 20% aqueous NaOH was added until the pH=13. The solution was extracted with dichloromethane (3×50 mL). The organic layers were combined, washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to provide a solid that was crystallized from acetonitrile. The crystals were dried under vacuum at 65° C. to provide 2-(ethoxymethyl)-1-({4-[2-(methylsulfonyl)ethoxy]piperidin-4-yl}methyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.25 g, 76%) as crystalline plates, mp 212-214° C. 1H NMR (300 MHz, DMSO-d6) δ 8.26 (d, J=8.1 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.44 (t, J=8.1 Hz, 1H), 7.26 (t, J=8.1 Hz, 1H), 6.61 (bs, 2H), 4.85 (s, 2H), 4.81 (s, 2H), 3.70 (t, J=5.6 Hz, 2H), 3.55 (q, J=7.5 Hz, 2H), 3.19 (t, J=5.6 Hz, 2H), 2.92 (s, 3H) 2.66-2.58 (m, 4H), 1.84 (bs, 1H), 1.70-1.66 (m, 2H), 1.48-1.38 (m, 2H), 1.16 (t, J=7.5 Hz, 3H); MS (APCI) m/z 462 (M+H)+; Anal. Cacld for C22H31N5O4S: C, 57.25; H, 6.77; N, 15.17. Found: C, 57.48; H, 7.05; N, 15.57.

Workup

  1. temperatureThe resulting yellow solution was heated
  2. temperatureat reflux for 1.5 h
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe resulting solid was dissolved in water (20 mL)
  5. addition20% aqueous NaOH was added until the pH=13
  6. extractionThe solution was extracted with dichloromethane (3×50 mL)
  7. washwashed with brine (50 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto provide a solid
  12. customthat was crystallized from acetonitrile
  13. customThe crystals were dried under vacuum at 65° C.

Sources & evidence

ORD record
ord-19313fef90a94007a6994c30109aa4b7
Source dataset
uspto-grants-2011_02
Patent number
US07884207B2

Reaction notes

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