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

HRID 1441476Notes

Reaction equation

HRID 1441476 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]([F:32])=[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:33]=[N:34][N:35]=[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]([F:32])=[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:35][N:34]=[N:33][N:9]23)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 1363420815-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

Product 1

HCID 1354245029-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanolYield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of intermediate 9 (0.0014 mol) in toluene (10 ml) was stirred and refluxed for 48 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 (0.4 g, 57%) was washed with diethyl ether. The precipitate was filtered off and dried under a vacuo, yielding 0.35 g (50%) of 9-(3-chlorophenyl)-α-(4-fluorophenyl)4,9-dihydro-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol (compound 2), mp. 180° C.

Workup

  1. temperaturerefluxed for 48 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. washThe residue (0.4 g, 57%) was washed with diethyl ether
  9. filtrationThe precipitate was filtered off
  10. customdried under a vacuo

Sources & evidence

ORD record
ord-2f9e5b521c39433ebdfe668587099298
Source dataset
uspto-grants-2010_02
Patent number
US07655654B2

Reaction notes

Loading…