O-Methylhydroxylamine hydrochloride → HCID 22936274, compound

HRID 387919Notes

Reaction equation

HRID 387919 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.[CH3:32][O:33][NH2:34]>>[CH3:32][O:33][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 methoxyamine 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-83ec74fa488c447a84fce86d80736e8a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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