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

HRID 513598노트

반응식

HRID 513598 반응식
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

참가 물질

4

반응물 2

HCID 10906Tert-Butyl nitriteHCID 167599312-Amino-4-fluoro-N-quinolin-8-yl-benzenesulfonamide2회

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
10 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-8cab3dc6a9a84c729abfa93246cfa1f0
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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