8-[4-(1,3-Dioxolan-2-yl)phenyl]-3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine → 4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde

HRID 1678743Notes

Reaction equation

HRID 1678743 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:18]4=[N:28][N:29]=[C:30]([CH3:31])[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1>O1CCOCC1.Cl>[CH3:31][C:30]1[N:17]2[C:18]([C:19]3[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:12]([C:9]4[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=4)=[N:13][C:14]=3[CH:15]=[CH:16]2)=[N:28][N:29]=1

Participants

4

Reactant 1

HCID 594729618-[4-(1,3-Dioxolan-2-yl)phenyl]-3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Product 1

HCID 594729414-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 8-[4-(1,3-dioxolan-2-yl)phenyl]-3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine (5-1, 0.30 g, 0.73 mmol) in dioxane (5 mL) and 3N HCl (5 mL) was stirred at room temperature for 15 min. The mixture was concentrated at 25° C. to remove most of the dioxane. The residue was poured into ice cold water to give a brown solid which was collected via filtration and dried with toluene (×2) azeotropically the give the title compound. LRMS m/z (M+1) Calcd: 365.1. Found 365.2.

Workup

  1. concentrationThe mixture was concentrated at 25° C.
  2. customto remove most of the dioxane
  3. additionThe residue was poured into ice cold water
  4. customto give a brown solid which
  5. filtrationwas collected via filtration
  6. dry with materialdried with toluene (×2) azeotropically the

Sources & evidence

ORD record
ord-fd209b9c69f6431d9c2251ee8cc045c5
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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