Sodium Hydroxide → HCID 11246952, compound

HRID 1351180Notes

Reaction equation

HRID 1351180 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:17]([NH2:19])=[C:16]([O:20][CH3:21])[C:15]([O:22][CH3:23])=[CH:14][C:13]=3[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[C:26](OC(=O)CC)(=O)[CH2:27][CH3:28]>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9]3[C:18]4[C:13]([N:12]=[CH:11][N:10]=3)=[CH:14][C:15]([O:22][CH3:23])=[C:16]([O:20][CH3:21])[C:17]=4[N:19]=[C:26]2[CH2:27][CH3:28])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 31263Propionic anhydrideHCID 21098407HCID 21098407, compound

Product 1

HCID 11246952HCID 11246952, compound

Procedure

A solution of N4-(3-bromo-phenyl)-6,7-dimethoxy-quinazoline-4,5-diamine (120 mg, 0.32 mmol) (from Example 6, Step B, supra) in propionic anhydride (3 mL) (Aldrich) was heated at 170° C. for 2 hours. Aqueous NaOH solution was added to the reaction mixture to a pH 10–12. The solution was extracted with chloroform (50 mL). The organic layer was separated, dried over Na2SO4, and concentrated. This residue was purified by chromatography using EtOAc/Et3N (1:0.05) as eluent to give the desired 3-(3-bromo-phenyl)-2-ethyl-8,9-dimethoxy-3H-1,3,4,6-tetraaza-phenalene as a brown solid. (Yield 50 mg, 38%).

Workup

  1. extractionThe solution was extracted with chloroform (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThis residue was purified by chromatography

Sources & evidence

ORD record
ord-26fc650688784e26a417d4b3c3d2e5dd
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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