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 347007ノート

反応式

HRID 347007 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9da5b9046a854b2092c8b2500049342d
出典データセット
uspto-grants-2007_02
特許番号
US07173040B2

反応ノート

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