O-Methylhydroxylamine hydrochloride → HCID 72448483, compound

HRID 1623105Notes

Reaction equation

HRID 1623105 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:25][CH2:26][CH2:27][CH3:28])[N:18]([CH2:19][CH2:20][CH2:21][C:22](=O)[CH3:23])[C:14]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1>CO>[CH3:3][O:2][N:4]=[C:22]([CH2:21][CH2:20][CH2:19][N:18]1[C:14]2[C:13]3[N:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=[C:17]1[CH2:25][CH2:26][CH2:27][CH3:28])[CH3:23]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 69507356HCID 69507356, compound

Product 1

HCID 72448483HCID 72448483, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methoxylamine hydrochloride (0.59 g, 21 mmol, 1.5 eq) was added to a solution of 5-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one (1.54 g, 4.73 mmol, 1 eq) in methanol (20 mL) and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (75 mL). The aqueous layer was extracted with dichloromethane (2×25 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a yellow solid. The material was subjected to HPFC (silica gel, eluting with 0-25% CMA in chloroform), triturated with hot acetonitrile, filtered, and dried at 100° C. under vacuum for 24 hours to afford 1.66 g of 5-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)pentan-2-one O-methyloxime as a white powder with an E/Z ratio of 80:20, mp 132-134° C. Anal. calcd for C19H26N6O: C, 64.38; H, 7.39; N, 23.71. Found: C, 64.19; H, 7.42; N, 23.76.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (100 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×25 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a yellow solid
  8. washThe material was subjected to HPFC (silica gel, eluting with 0-25% CMA in chloroform)
  9. customtriturated with hot acetonitrile
  10. filtrationfiltered
  11. customdried at 100° C. under vacuum for 24 hours

Sources & evidence

ORD record
ord-01d443765ebf46d9bdb15d0c37cade96
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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