Tetrahydrofuran → 6-(2-(1-Iminobutyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine

HRID 1028959Notes

Reaction equation

HRID 1028959 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.[CH2:27]([Mg]Br)[CH2:28][CH3:29].C1COCC1>>[NH:21]=[C:20]([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)[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 673450552-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrileHCID 178455851HCID 178455851, compound

Product 1

HCID 533288206-(2-(1-Iminobutyl)-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 (0.040 g, 0.116 mmol) under N2 atmosphere was added a solution of propylmagnesium bromide, 2.0M in THF (0.232 mL, 0.465 mmol) via syringe at ambient temperature. The mixture was sonicated until all solids were in solution and then warmed vessel to 60° C. for 7 h. The mixture was concentrated, diluted with MeOH and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford 6-(2-(1-iminobutyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine as white solid. MS (ESI, pos. ion) m/z: 389 (M+1).

Workup

  1. customThe mixture was sonicated until all solids
  2. concentrationThe mixture was concentrated
  3. additiondiluted with MeOH
  4. custompurified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-abb2a01ff69b40e9a7ec672e4057dc8a
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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