Hydrochloric Acid → HCID 10270339, compound

HRID 432738Notes

Reaction equation

HRID 432738 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH:15]([CH2:33][CH3:34])[CH2:16][O:17][CH2:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>>[NH:23]1[CH2:24][CH2:25][CH:20]([CH2:19][CH2:18][O:17][CH2:16][CH:15]([N:14]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[CH:13]2)[CH2:33][CH3:34])[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21898036HCID 21898036, compound

Product 1

HCID 10270339HCID 10270339, compoundYield 64.8%

Procedure

Under a nitrogen atmosphere, tert-butyl 4-{2-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butoxy]ethyl}piperidine-1-carboxylate (1.00 g, 2.1 mmol) and 2N ethanolic hydrochloric acid (10 ml, 20 mmol) were combined and the solution was stirred at ambient temperature for 14 hours. The solvent was removed in vacuo and the resulting tan solid was dissolved in water. Saturated aqueous sodium carbonate was added until the pH reached 10. After extraction with dichloromethane (3×), the organic fractions were combined, washed with brine, dried (Na2SO4), filtered, and the majority of the solvent was removed in vacuo. Hexane was added to form a precipitate. Vacuum filtration yielded 0.5 g of 1-{1-[(2-piperidin-4-ylethoxy)methyl]propyl}-1H-imidazo[4,5-c]quinolin-4-amine as a tan powder. 1H-NMR (300 MHz, DMSO-d6): δ8.34 (bs, 1H), 8.19 (d, J=8.49 Hz, 1H), 7.61 (dd, J=8.31, 1.13 Hz, 1H), 7.45-7.39 (m, 1H), 7.25-7.19 (m, 1H), 6.55 (s, 2H), 5.25-5.15 (m, 1H), 4.00-3.80 (m, 2H), 3.5-3.3 (m, 2H), 2.8-2.64 (m, 2H), 2.22-2.11 (m, 2H), 2.09-1.99 (m, 2H), 1.8-1.63 (bs, 1H), 1.37-1.0 (m, 5H), 0.95-0.7 (m, 5H); 13C-NMR (75 MHz, DMSO-d6): δ152.8, 145.8, 140.6, 133.0, 127.8, 127.0, 126.9, 121.3, 121.0, 115.5, 71.8, 68.1, 58.4, 46.1, 36.3, 33.1, 32.7, 24.5, 9.9; MS (CI) m/e 368.2459 (368.2450 calcd for C21H30N5O).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting tan solid was dissolved in water
  3. additionSaturated aqueous sodium carbonate was added until the pH
  4. extractionAfter extraction with dichloromethane (3×)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe majority of the solvent was removed in vacuo
  9. additionHexane was added
  10. customto form a precipitate
  11. filtrationVacuum filtration

Sources & evidence

ORD record
ord-2b53212b41984fbc8085b436b3919d83
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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