Sodium cyanoborohydride → HCID 86612266, compound

HRID 1623203Notes

Reaction equation

HRID 1623203 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[CH3:26]>C(O)C.C(O)(=O)C>[CH3:5][O:6][NH:7][CH2:8][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[CH3:26]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 72448476HCID 72448476, compound

Product 1

HCID 86612266HCID 86612266, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent

Procedure

Sodium cyanoborohydride (16.0 g, 254 mmol) was added to a solution of 4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal O-methyloxime (prepared as described in Example 45, 15.1 g, 50.8 mmol) in ethanol (100 mL) and acetic acid (15 mL). The reaction mixture was stirred at room temperature for 2 hours, additional acetic acid (15 mL) was added, and stirring was continued for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and adjusted to pH 7 with saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated to provide 12.1 g of 1-[4-(methoxyamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionThe mixture was extracted with dichloromethane
  6. washwashed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9728c76b92be45749199d9e2afcf02ad
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

Loading…