Hydroxylamine HCl → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone oxime

HRID 1028962Notes

Reaction equation

HRID 1028962 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-].[OH:34][NH3+:35]>CO.N1C=CC=CC=1>[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:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:35][OH:34])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 21645Hydroxylamine HClHCID 67325753(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

Product 1

HCID 76012307(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone 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, prepared as Example 15, Step 1) in MeOH (4.0 mL) was added hydroxyammonium chloride (0.044 mL, 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, 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 oxime as a off-white solid. MS (ESI, pos. ion) m/z: 439 (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-6f6aba44208b42a7bf6f171d96bd251e
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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