Tetrahydrofuran → 6-(2-(Imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028963Notes

Reaction equation

HRID 1028963 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:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])[CH:8]=2)[N:3]=1.[C:27]1([Mg]Cl)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1COCC1>>[NH:21]=[C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]1[CH:22]=[CH:23][CH:24]=[C:25]([CH3:26])[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

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 673450552-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 866768386-(2-(Imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

Conditions

Temperature
60 °C

Procedure

To a sealed vessel containing 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile (0.10 g, 0.290 mmol, prepared as in Example 14, Step 1) was added phenylmagnesium chloride, 2.0M solution in THF (0.58 mL, 1.161 mmol). The mixture was sonicated until all solids were in solution and then warmed vessel to 60° C. for 15 h. The reaction mixture was cooled to RT and divided into two portions. The imine solution was concentrated in vacuo. The residue was taken up in 2.5 mL MeOH and purified by HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford 6-(2-(imino(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine.

Workup

  1. customThe mixture was sonicated until all solids
  2. temperatureThe reaction mixture was cooled to RT
  3. concentrationThe imine solution was concentrated in vacuo
  4. custompurified by HPLC (10-100% MeCN/H2O with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-888960ec750149b9b8d696ca492295b4
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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