Hydrochloric Acid → HCID 22499017, compound

HRID 1814912Notes

Reaction equation

HRID 1814912 reaction equation
C([BH3-])#N.[Na+].[N:5](=[C:7]([CH3:25])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14])[OH:6].Cl>CO.CCOCC>[OH:6][NH:5][CH:7]([CH3:25])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 86584511HCID 86584511, compound

Product 1

HCID 22499017HCID 22499017, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium cyanoborohydride (62.84 mg, 1 mmol) was added to a solution of 1-(5-oximinohexyl)-3,7-dimethylxanthine (Klein, J. P.; Leigh, A. Oxime Substituted Therapeutic Compounds, U.S. Pat. No. 5,770,595 (Jun. 23, 1998)) (293 mg, 1 mmol) in methanol (10 ml). 1 M hydrogen chloride in ether was added to pH 4-5. After stirring for 3 hours, the mixture was concentrated under reduced pressure. 1 N aqueous sodium hydroxide solution to pH 9-10 (10 ml). The mixture was extracted with 10% methanol-dichloromethane (3×50 ml). The combined extracts were washed with water (50 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 10% methanol-dichloromethane to provide 1-(5-(N-hydroxy)aminohexyl)-3,7-dimethylxanthine (180 mg).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe mixture was extracted with 10% methanol-dichloromethane (3×50 ml)
  3. washThe combined extracts were washed with water (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel eluting with 10% methanol-dichloromethane

Sources & evidence

ORD record
ord-abbe660f26be44b18fe395486b3d5830
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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