Acetic Acid → HCID 86612249, compound

HRID 1623116Notes

Reaction equation

HRID 1623116 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][N:7]=[CH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[C:16]([NH2:25])[C:15]=2[N:14]=[C:13]1[CH2:26][CH2:27][CH3:28].C(O)(=O)C.[OH-].[Na+]>C(O)C>[NH2:25][C:16]1[C:15]2[N:14]=[C:13]([CH2:26][CH2:27][CH3:28])[N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][O:6][CH3:5])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86612248HCID 86612248, compound

Product 1

HCID 86612249HCID 86612249, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium cyanoborohydride (5.40 g, 86 mmol) was added to a mixture of 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime (5.60 g, 17.2 mmol), acetic acid (30 mL), and ethanol (75 mL) and stirred for 1 hour. The reaction mixture was cooled to 0° C. and the pH was adjusted to 8 with 25% sodium hydroxide solution. The reaction mixture was then concentrated under reduced pressure and diluted with dichloromethane (200 mL) and saturated aqueous sodium bicarbonate solution (75 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×75 mL). The combined organics were washed with water (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 5.2 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-O-methyl-hydroxylamine as a light brown solid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additiondiluted with dichloromethane (200 mL) and saturated aqueous sodium bicarbonate solution (75 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×75 mL)
  5. washThe combined organics were washed with water (2×50 mL)
  6. dry with materialdried over potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1431e565f4a947fab1177bf29ee3fb66
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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