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

HRID 513595노트

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HRID 513595 반응식
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

참가 물질

4

반응물 2

HCID 10906Tert-Butyl nitriteHCID 10701592-Amino-N-quinolin-8-yl-benzenesulfonamide2회

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
10 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-61c5a7d4b32d41a0a398ec1bff7d4eb4
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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