Acetone → HCID 58835285, compound

HRID 1187401Notes

Reaction equation

HRID 1187401 reaction equation
[CH3:1][C:2]([CH3:4])=O.[NH2:5][O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[CH:11]1>CO>[NH2:23][C:14]1[C:13]2[N:12]=[CH:11][N:10]([CH2:9][CH2:8][CH2:7][O:6][N:5]=[C:2]([CH3:4])[CH3:1])[C:22]=2[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 69192223HCID 69192223, compound

Product 1

HCID 58835285HCID 58835285, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetone (1 mL) was added to a suspension of 1-[3-(aminooxy)propyl]-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (0.237 g, 0.92 mmol) in methanol (6 mL) at room temperature. The mixture was stirred and eventually a solution formed. After 6 hours, the volatiles were removed and the crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-25% CMA in chloroform) to give a white powder that was crystallized from acetonitrile to yield 0.110 g of acetone O-[3-(4-amino-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl]oxime as white needles, mp 120-121° C.

Workup

  1. customeventually a solution formed
  2. customthe volatiles were removed
  3. customthe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-25% CMA in chloroform)
  4. customto give a white powder that
  5. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-64ac0354a84241e0abdab6ca78beabd0
Source dataset
uspto-grants-2014_03
Patent number
US08673932B2

Reaction notes

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