Diisopropylethylamine → N-{1-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethyl}-9H-purin-6-amine

HRID 1192563Notes

Reaction equation

HRID 1192563 reaction equation
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:19]([CH:29]([NH2:31])[CH3:30])=[CH:20][C:21]([CH3:28])=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[CH:15]=[CH:16][CH:17]=1.C(N(CC)C(C)C)(C)C>C(O)C>[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:19]([CH:29]([NH:31][C:2]3[N:10]=[CH:9][N:8]=[C:7]4[C:3]=3[N:4]=[CH:5][NH:6]4)[CH3:30])=[CH:20][C:21]([CH3:28])=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 583686281-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanamineHCID 178419477HCID 178419477, compound

Product 1

HCID 178425523N-{1-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethyl}-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-bromo-9H-purine (0.0712 g, 0.358 mmol), 1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethanamine (0.050 g, 0.18 mmol), and N,N-diisopropylethylamine (0.0623 mL, 0.358 mmol) in ethanol (0.6 mL) was heated at reflux under nitrogen overnight. The mixture was evaporated and the resulting residue was purified on a RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the product. LCMS calculated for C23H20FN6 (M+H)+: m/z=399.2; Found: 399.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen overnight
  3. customThe mixture was evaporated
  4. customthe resulting residue was purified on a RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)
  6. customto give the product

Sources & evidence

ORD record
ord-1b1b8902ab6847a198655510a78ed150
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…