Tert-Butyl nitrite → 9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513598ノート

反応式

HRID 513598 の反応式
N[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][CH:19]=[CH:18]2)(=[O:11])=[O:10].C(ON=O)(C)(C)C>C(O)(=O)C>[F:8][C:6]1[CH:5]=[C:4]2[C:3]([S:9](=[O:11])(=[O:10])[NH:12][C:13]3[C:14]2=[CH:15][CH:16]=[C:17]2[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]2)=[CH:2][CH:7]=1

参加物

4

反応物 2

HCID 10906Tert-Butyl nitriteHCID 167599312-Amino-4-fluoro-N-quinolin-8-yl-benzenesulfonamide2 回

生成物 1

HCID 167599219-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide収率 2.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
10 °C

実験手順

2-Amino-4-fluoro-N-quinolin-8-yl-benzenesulfonamide (Example Compound 31) (315 mg, 0.99 mmol) was suspended in acetic acid (4 ml) and cooled to 10° C. Tert-butylnitrite (177 μl, 1.49 mmol) was added and the reaction was warmed to room temperature over 10 min. The reaction was quenched water (5 ml) and the resulting solution was concentrated in vacuo. The crude residue was dissolved in acetic acid (2 ml) and irradiated at 120° C. for 10 mins in the microwave. After cooling, the reaction was concentrated in vacuo. The crude residue was purified by preparative HPLC (acidic conditions) to give the title compound (7 mg, 2%).

後処理

  1. temperaturethe reaction was warmed to room temperature over 10 min
  2. customThe reaction was quenched water (5 ml)
  3. concentrationthe resulting solution was concentrated in vacuo
  4. dissolutionThe crude residue was dissolved in acetic acid (2 ml)
  5. customirradiated at 120° C. for 10 mins in the microwave
  6. temperatureAfter cooling
  7. concentrationthe reaction was concentrated in vacuo
  8. customThe crude residue was purified by preparative HPLC (acidic conditions)

出典と根拠

ORDレコード
ord-8cab3dc6a9a84c729abfa93246cfa1f0
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

読み込み中…