5-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine → 5-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine

HRID 347007Notes

Reaction equation

HRID 347007 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)([C:20]4[N:24]([CH3:25])[C:23](SC)=[N:22][N:21]=4)[NH2:19])[CH:16]=3)[N:11]3[N:35]=[N:36][N:37]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1>[Ni].CC(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][N:21]=4)[NH2:19])[CH:16]=3)[N:11]3[N:35]=[N:36][N:37]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 210820625-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine

Product 1

HCID 210820015-(3-chlorophenyl)-alpha-(4-chlorophenyl)-alpha-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamineYield 18.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 180AcetoneSolvent

Procedure

Raney nickel (6.5 g) was added to a solution of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine (0.0012 mol) in 2-propanone (30 ml) under N2 flow. The mixture was stirred at room temperature for 1 hour and 30 minutes, filtered over celite and rinsed with CH2Cl2/CH3OH. The solvent was evaporated. The residue was taken up in DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 96/4/0.5; 15–35 μm). The pure fractions were collected and the solvent was evaporated The residue was crystallized from CH3CN/diethyl ether. The precipitate was filtered off and dried, yielding 0.11 g (18%) of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine, mp. 220° C.

Workup

  1. filtrationfiltered over celite
  2. washrinsed with CH2Cl2/CH3OH
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue (0.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 96/4/0.5; 15–35 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated The residue
  11. customwas crystallized from CH3CN/diethyl ether
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-9da5b9046a854b2092c8b2500049342d
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

Loading…