Sodium cyanoborohydride → HCID 86612257, compound

HRID 1623138Notes

Reaction equation

HRID 1623138 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][N:7]=[C:8]([CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][C:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:20][C:19]=3[N:18]=[C:17]([NH2:32])[C:16]=2[N:15]=[C:14]1[CH2:33][CH2:34][CH3:35])[CH3:9]>C(O)C.C(O)(=O)C>[NH2:32][C:17]1[C:16]2[N:15]=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]([CH2:12][CH2:11][CH2:10][CH:8]([NH:7][O:6][CH3:5])[CH3:9])[C:25]=2[C:24]2[CH:23]=[CH:22][C:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:20][C:19]=2[N:18]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 58869106HCID 58869106, compound

Product 1

HCID 86612257HCID 86612257, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Sodium cyanoborohydride (2.26 g, 36.1 mmol) was added to a solution of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime (3.0 g, 7.22 mmol) in ethanol (50 mL) and acetic acid (3 mL) and stirred at ambient temperature overnight. Another portion of sodium cyanoborohydride was added (1.0 g) and the reaction was stirred for an additional 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted in water and neutralized to pH ˜8 with 10% sodium hydroxide solution. The product was extracted into dichloromethane, washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure to provide 2.73 g of N-[4-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-O-methylhydroxylamine.

Workup

  1. stirringthe reaction was stirred for an additional 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted in water and neutralized to pH ˜8 with 10% sodium hydroxide solution
  4. extractionThe product was extracted into dichloromethane
  5. washwashed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b46813cf7d88497c9acc2e89612eb4ec
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…