Acetic Acid → HCID 59130469, compound

HRID 1992600Notes

Reaction equation

HRID 1992600 reaction equation
C(O)(=O)C.C([BH3-])#N.[Na+].O1CCCC1.[NH2:14][C:15]1[C:24]2[N:25]=[C:26]([CH2:36][CH2:37][CH3:38])[N:27]([CH2:28][CH2:29][CH2:30][O:31][N:32]=[C:33]([CH3:35])[CH3:34])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1>CO>[CH:33]([NH:32][O:31][CH2:30][CH2:29][CH2:28][N:27]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:14])[C:24]=2[N:25]=[C:26]1[CH2:36][CH2:37][CH3:38])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 58835277HCID 58835277, compound

Product 1

HCID 59130469HCID 59130469, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (10 mL) followed by 1 M sodium cyanoborohydride in tetrahydrofuran (11.05 mL, 11.05 mmol) was added to a stirred solution of acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime (1.50 g, 4.42 mmol) in methanol (10 mL). The reaction was stirred overnight at room temperature and then was concentrated under reduced pressure. The residue was diluted with water (100 mL) and the pH was adjusted with solid sodium hydroxide to pH 6. The mixture was extracted with chloroform (2×100 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 1.31 g of 1-{3-[(isopropylamino)oxy]propyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe residue was diluted with water (100 mL)
  3. extractionThe mixture was extracted with chloroform (2×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6c04c0b4664486fb2aed40ed09eb257
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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