Acetone → 6-(2-(Amino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028964Notes

Reaction equation

HRID 1028964 reaction equation
[NH:1]=[C:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([NH2:20])[C:14]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[CH:13]2.[BH4-].[Na+].CC(C)=O>CO>[NH2:1][CH:2]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([NH2:20])[C:14]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)=[CH:13]2

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 866768386-(2-(Imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Product 1

HCID 533288236-(2-(Amino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (ice bath) solution of 6-(2-(imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine (0.058 g, 0.137 mmol) in MeOH (5.0 mL) was added sodium borohydride, 99% (0.033 mL, 0.925 mmol). The mixture was then warmed to RT and stirred for 1 h. The excess NaBH4 was then treated with acetone. The resulted solution was concentrated and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford 6-(2-(amino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine as white solid. MS (ESI, pos. ion) m/z: 425 (M+1).

Workup

  1. concentrationThe resulted solution was concentrated
  2. custompurified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-f2edd59c31ef4d9faec09fa3f371489d
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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