5-(3-chlorophenyl)-4,5-dihydro-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol → 9-(3-chlorophenyl)-4,9-dihydro-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol

HRID 1788068Notes

Reaction equation

HRID 1788068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:16]=3)[N:11]3[N:34]=[N:35][N:36]=[C:10]3[NH:9]2)[CH:5]=[CH:6][CH:7]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[CH:16]=[C:15]([C:18]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[OH:19])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]3=[N:36][N:35]=[N:34][N:9]23)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 1363420825-(3-chlorophenyl)-4,5-dihydro-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

Product 1

HCID 1360964249-(3-chlorophenyl)-4,9-dihydro-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanolYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of intermediate 17 (0.0006 mol) in toluene (10 ml) was stirred and refluxed for 5 hours, then brought to room temperature and the solvent, was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.5). The pure fractions were collected and the solvent was evaporated. The residue (0.12 g, 40%) was taken up in DCM. The solvent was evaporated till dryness, yielding 0.08 g (27%) of 9-(3-chlorophenyl)-4,9-dihydro-α-(4-methoxyphenyl)-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol (compound 3).

Workup

  1. temperaturerefluxed for 5 hours
  2. custombrought to room temperature
  3. customthe solvent, was evaporated till dryness
  4. customThe solvent was evaporated till dryness
  5. customThe residue was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH/Et3N 95/5/0.5)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-ee20223f472244bfac1603ceaa338f24
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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