O-Methylhydroxylamine hydrochloride → HCID 22936274, compound

HRID 1010312Notes

Reaction equation

HRID 1010312 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:29]=[CH:28][C:11]([O:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([C:23]([OH:25])=O)[CH:21]=4)[N:16]=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH3:30])=[O:6])[CH2:3][CH2:2]1.Cl.[O:32]([NH2:34])[CH3:33]>>[CH3:33][O:32][NH:34][C:23]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:26][CH3:27])[N:16]=[CH:15][CH:14]=[C:13]2[O:12][C:11]1[CH:28]=[CH:29][C:8]([NH:7][C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:6])=[C:9]([CH3:30])[CH:10]=1)=[O:25]

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 22936426HCID 22936426, compound

Product 1

HCID 22936274HCID 22936274, compoundYield 21.74%

Procedure

4-(4-((Cyclopropylamino)carbonyl)amino-3-methylphenoxy)-7-methoxy-6-quinolinecarboxylic acid (30 mg, 0.0736 mmol) and methoxylamine hydrochloride (0.0123 ml) were used for reaction in the same manner as Example 458, and after purification by NH silica gel column chromatography (ethyl acetate:methanol=10:1), the obtained crystals were suspended in ethanol, diluted with hexane, filtered out, washed with hexane and dried by aspiration to obtain the title compound (7 mg, 0.0160 mmol, 21.74%) as light yellow crystals.

Workup

  1. customafter purification by NH silica gel column chromatography (ethyl acetate:methanol=10:1)
  2. additiondiluted with hexane
  3. filtrationfiltered out
  4. washwashed with hexane
  5. customdried by aspiration

Sources & evidence

ORD record
ord-433a85be98da4aea8924e8a6a3cb327c
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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