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

HRID 1441473
ノート
印刷プレビュー

反応式

HRID 1441473 の反応式
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:28]3[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=3)([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[N-:34]=[N+:35]=[N-:36].[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:28]4[N:32]([CH3:33])[CH:31]=[N:30][CH:29]=4)([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[OH:20])[CH:8]=3)[N:3]3[N:34]=[N:35][N:36]=[C:2]3[N:11]=2)[CH:17]=[CH:16][CH:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 179761062-chloro-4-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-6-quinazolinemethanol

生成物 1

HCID 686877095-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol収率 72.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of intermediate 24 (0.0105 mol) and sodium azide (0.031 mol) in DMF (70 ml) was stirred at 90° C. for 2 hours then cooled and poured out into ice water. The precipitate was filtered 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: DCM/MeOH/NH4OH; 95/5/0.1). The pure fractions were collected and the solvent was evaporated, yielding 3.68 g (quantitative) of 5-(3-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-α-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 25), mp. 200° C.

後処理

  1. temperaturethen cooled
  2. filtrationThe precipitate was filtered
  3. washThe organic layer was washed with water
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-61f19487dd8e40aab1e2b1437fdf0084
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07655654B2

反応ノート

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