O-Methylhydroxylamine hydrochloride → (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone O-methyl oxime

HRID 1028961Notes

Reaction equation

HRID 1028961 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=O)[CH:8]=2)[N:3]=1.Cl.[O:34]([NH2:36])[CH3:35]>CO.N1C=CC=CC=1>[CH3:35][O:34][N:36]=[C:25]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:18]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:1])[C:11]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[CH:10]2)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 67325753(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

Product 1

HCID 76012306(2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone O-methyl oxime

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (0.090 g, 0.213 mmol) in MeOH (4.0 mL) was added methoxylamine hydrochloride, 98% (0.089 g, 1.063 mmol) followed by 3 drops of pyridine. The reaction mixture was brought up to reflux for 41 h until the conversion was completed, as determined by LCMS. The reaction mixture was cooled to RT and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA) to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone O-methyl oxime as a off-white solid. MS (ESI, pos. ion) m/z: 453 (M+1).

Workup

  1. temperatureto reflux for 41 h until the conversion
  2. custompurified on HPLC (10-100% MeCN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-0eefab9ff0ee4939a9162c14b0bfb3b1
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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