2-Cyano-3-cyclobutyloxy-4,5-dimethoxyaniline → 2-Cyclobutyloxy-3,4-dimethoxy-6-[1-(5,6,7,8-tetrahydro-1,6-naphthyridin-6-yl)ethylideneamino]benzonitrile

HRID 2228514Notes

Reaction equation

HRID 2228514 reaction equation
[C:1]([C:3]1[C:9]([O:10][CH:11]2[CH2:14][CH2:13][CH2:12]2)=[C:8]([O:15][CH3:16])[C:7]([O:17][CH3:18])=[CH:6][C:4]=1[NH2:5])#[N:2].[C:19]([N:22]1[CH2:31][CH2:30][C:29]2[N:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:23]1)(=O)[CH3:20]>>[NH3:2].[CH:11]1([O:10][C:9]2[C:8]([O:15][CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=[C:4]([N:5]=[C:19]([N:22]3[CH2:31][CH2:30][C:29]4[N:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:23]3)[CH3:20])[C:3]=2[C:1]#[N:2])[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 184706542-Cyano-3-cyclobutyloxy-4,5-dimethoxyanilineHCID 187651916-Acetyl-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 2

HCID 222AmmoniaHCID 184706302-Cyclobutyloxy-3,4-dimethoxy-6-[1-(5,6,7,8-tetrahydro-1,6-naphthyridin-6-yl)ethylideneamino]benzonitrileYield 48%

Procedure

The subtitle compound was prepared from 2-cyano-3-cyclobutyloxy-4,5-dimethoxyaniline and 6-acetyl-5,6,7,8-tetrahydro-1,6-naphthyridine following the procedure described in Example 10(g), allowing the reaction to reflux for 3 hours. The crude product was purified on silica gel eluting with ethyl acetate:methanol:0.880 aqueous ammonia solution (95:5:1, v/v) to give the subtitle compound as a gum (382 mg, 48%). Rf 0.53 (dichloromethane: methanol:0.880 aqueous ammonia 90:10:1, v/v). MS m/z 407 (MH)+.

Workup

  1. customthe reaction
  2. temperatureto reflux for 3 hours
  3. customThe crude product was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-4460e420670147889b014e0cbc5f315d
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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