Sodium Azide → 5-(3-chlorophenyl)-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

HRID 1788054Notes

Reaction equation

HRID 1788054 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)([C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[OH:20])[CH:8]=3)[N:3]3[N:35]=[N:36][N:37]=[C:2]3[N:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 179761132-chloro-4-(3-chlorophenyl)-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-6-quinazolinemethanol

Product 1

HCID 688609185-(3-chlorophenyl)-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanolYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of intermediate 15 (0.0224 mol) and sodium azide (0.067 mol) in DMF (120 ml) was stirred at 90° C. for 2 hours, brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in DCM. The organic layer was washed with water, separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: toluene/iPrOH/NH4OH 90/10/1). The pure fractions were collected and the solvent was evaporated, yielding 9 g (80%) of 5-(3-chlorophenyl)-α-(4-methoxyphenyl)-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 16), mp 200° C.

Workup

  1. custombrought to room temperature
  2. stirringstirred
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. washThe organic layer was washed with water
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by column chromatography over silica gel (15-40 μm) (eluent: toluene/iPrOH/NH4OH 90/10/1)
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3174410cc7aa4d319705df78235927e0
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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