2,4-Dimethoxybenzylamine → 4-(2,4-Dimethoxy-benzylamino)-isoquinoline-1-carbonitrile

HRID 2378424Notes

Reaction equation

HRID 2378424 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[N:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19]>C(#N)C>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 218749014-Bromoisoquinoline-1-carbonitrile

Product 1

HCID 218754144-(2,4-Dimethoxy-benzylamino)-isoquinoline-1-carbonitrileYield 30.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of compound 470B (699 mg, 3.00 mmol) and 2,4-dimethoxybenzylamine (4.8 mL, 30 mmol) in 15 mL of acetonitrile was refluxed for 16 h. After concentration in vacuo, the residue was purified on a 5×15 cm silica gel column, eluting with 3:2 hexane:ethyl acetate to afford 290 mg (30%) of 470C as a light yellow solid. HPLC: 1.76 min (retention time) (Phenomenex C-18, 5 micron column, 4.6×30 mm, eluting with 10-90% aqueous methanol over 2 mincontaining 0.1% TFA, 4 mL/min, monitoring at 254 nm).

Workup

  1. temperaturewas refluxed for 16 h
  2. concentrationAfter concentration in vacuo
  3. customthe residue was purified on a 5×15 cm silica gel column
  4. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-0c6f87b237b1482c873f545b966e88db
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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