Acetone → HCID 57576705, compound

HRID 599441Notes

Reaction equation

HRID 599441 reaction equation
CO.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][NH2:24])[N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.[CH3:25][C:26]([CH3:28])=O>>[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][N:24]=[C:26]([CH3:28])[CH3:25])[N:16]([CH2:17][C:18]([OH:20])([CH3:19])[CH3:21])[C:12]=2[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 67052379HCID 67052379, compound

Product 1

HCID 57576705HCID 57576705, compound

Procedure

Methanol (21 mL) and acetone (2.6 mL) were added to 1-{4-amino-2-[(aminooxy)methyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}-2-methylpropan-2-ol (1.31 g, 4.3 mmol). The reaction was stirred for 15 minutes then concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, eluted with 0.7% methanol in chloroform) followed by recrystallization from acetonitrile/water to yield 0.56 g of acetone O-{[4-amino-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]-1,5-naphthyridin-2-yl]methyl}oxime as a white solid, mp 198-200° C.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe crude product was purified by flash chromatography (silica gel, eluted with 0.7% methanol in chloroform)
  3. customfollowed by recrystallization from acetonitrile/water

Sources & evidence

ORD record
ord-01e04fa938a04a4b8826fce99d070095
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

Loading…