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Pyridine → Trifluoromethylsulphonyloxyquinazoline

HRID 2227927
ノート
印刷プレビュー

反応式

HRID 2227927 の反応式
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].ClN([C:25]1[C:34]2[C:29](=[CH:30][C:31](O)=[C:32](OC)[CH:33]=2)[N:28]=[CH:27][N:26]=1)C1C=CC=CC=1F.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:27]1[N:26]=[CH:25][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)(=[O:5])=[O:4]
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

5

反応物 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1359906824-(Chloro-2-fluoroanilino)7-hydroxy-6-methoxyquinazoline

生成物 1

HCID 53804830Trifluoromethylsulphonyloxyquinazoline収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trifluoromethanesulphonic anhydride (0.55 ml, 3.3 mmol) was added to a stirred suspension of 4-(chloro-2-fluoroanilino)-7-hydroxy-6methoxyquinazoline (959 mg, 3 mmol), (prepared as described for the starting material in Example 2), in methylene chloride (2.2 ml) and pyridine (2.2 ml) under argon at 0° C. The reaction mixture was stirred for 1 hour at 0° C., allowed to warm to ambient temperature and stirred for a further 1.5 hours. The volatiles were removed by evaporation, the residue was dissolved in ethyl acetate, washed with dilute hydrochloric acid and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether/petroleum ether to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(trifluoromethylsulphonyloxyquinazoline (270 mg, 60%) as a beige solid.

後処理

  1. custom(prepared
  2. customat 0° C
  3. temperatureto warm to ambient temperature
  4. stirringstirred for a further 1.5 hours
  5. customThe volatiles were removed by evaporation
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with dilute hydrochloric acid and brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was triturated with ether/petroleum ether

出典と根拠

ORDレコード
ord-3da416b489a040ff97431edc65ec9566
出典データセット
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06414148B1

反応ノート

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