Ethyl Acetate → 6-(2-Benzyl-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028966Notes

Reaction equation

HRID 1028966 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[CH:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)O)[CH:8]=2)[N:3]=1.C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-].[Pd]>[CH2:25]([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

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67350995(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

Product 1

HCID 533289926-(2-Benzyl-6-methylphenyl)-3-morpholinoquinolin-2-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol (0.245 g, 0.576 mmol) and palladium hydroxide, 20 wt % Pd (dry basis) on carbon, wet (0.380 g, 2.71 mmol) in ethanol (15 mL) and ethyl acetate (5.0 mL) was stirred under H2 balloon overnight. 400 mg more Pd(OH)2 was added and stirred for 72 h. The product mixture was filtered through a pad of celite. The filtrate was concentrated and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA) to afford 6-(2-benzyl-6-methylphenyl)-3-morpholinoquinolin-2-amine as white solid. MS (ESI, pos. ion) m/z: 410 (M+1).

Workup

  1. filtrationThe product mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified on HPLC (10-100% MeCN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-54ea88f2e43349b29bcbb3da9323a0c3
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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