Tert-Butyl nitrite → 5H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxide

HRID 513595ノート

反応式

HRID 513595 の反応式
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O>C(O)(=O)C>[CH:17]1[C:16]2[C:21](=[C:12]3[C:13](=[CH:14][CH:15]=2)[C:4]2[C:3](=[CH:2][CH:7]=[CH:6][CH:5]=2)[S:8](=[O:10])(=[O:9])[NH:11]3)[N:20]=[CH:19][CH:18]=1

参加物

4

反応物 2

HCID 10906Tert-Butyl nitriteHCID 10701592-Amino-N-quinolin-8-yl-benzenesulfonamide2 回

生成物 1

HCID 6591015H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxide収率 55.3%

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-N-(quinolin-8-yl)-benzenesulfonamide (Example Compound 8) (100 mg, 0.32 mmol) was dissolved in acetic acid (2 ml) and stirred at 10° C. for 5 min. The solution was cooled to −10° C. before tert-butyl nitrite (36 μl, 0.08 mmol) was added dropwise, the mixture was allowed to warm to room temperature and stirred for 10 minutes. The reaction was quenched with water and extracted with EtOAc. The organic phase was washed with a sat. sodium bicarbonate solution, brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with MeOH/DCM/NH3 (1:100:2 drops) as the eluent to give the title compound (50 mg, 53%).

後処理

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. stirringstirred for 10 minutes
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. washThe organic phase was washed with a sat. sodium bicarbonate solution, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography with MeOH/DCM/NH3 (1:100:2 drops) as the eluent

出典と根拠

ORDレコード
ord-61c5a7d4b32d41a0a398ec1bff7d4eb4
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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