Hydrochloric Acid → 4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde

HRID 1678775Notes

Reaction equation

HRID 1678775 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]([C:31]5[N:32]=[CH:33][N:34]([CH3:36])[CH:35]=5)[N:17]4[CH:16]=[CH:15][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.Cl>C1COCC1>[CH3:36][N:34]1[CH:35]=[C:31]([C:30]2[N:17]3[C:18]([C:19]4[CH:20]=[C:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:12]([C:9]5[CH:10]=[CH:11][C:6]([CH:2]=[O:1])=[CH:7][CH:8]=5)=[N:13][C:14]=4[CH:15]=[CH:16]3)=[N:28][N:29]=2)[N:32]=[CH:33]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594729458-[4-(1,3-dioxolan-2-yl)phenyl]-3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Product 1

HCID 594728924-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 13-1 (2 g, 4.2 mMol) in THF (32 mL) was added 1N HCl (32 mL). A suspension developed as the reaction stirred at room temperature for 1 hour. The reaction was then quenched with 100 mL of a saturated NaHCO3 solution. The suspension was filtered and washed with water. The collected solid was dried azeotropically with toluene three times to yield 13-2 as a tan solid. Mass (M+1) calculated: 431.1615 observed: 431.1616

Workup

  1. customThe reaction was then quenched with 100 mL of a saturated NaHCO3 solution
  2. filtrationThe suspension was filtered
  3. washwashed with water
  4. dry with materialThe collected solid was dried azeotropically with toluene three times

Sources & evidence

ORD record
ord-3628087771c34e27ac5a53334143fde1
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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