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

HRID 513599노트

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HRID 513599 반응식
N[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)(=[O:14])=[O:13].C(ON=O)(C)(C)C>C(O)(=O)C.C1COCC1>[F:9][C:8]([F:10])([F:11])[C:6]1[CH:5]=[C:4]2[C:3]([S:12](=[O:14])(=[O:13])[NH:15][C:16]3[C:17]2=[CH:18][CH:19]=[C:20]2[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]2)=[CH:2][CH:7]=1

참가 물질

4

반응물 2

HCID 10906Tert-Butyl nitriteHCID 167595482-Amino-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide2회

생성물 1

HCID 167599099-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide수율 23%

시약·촉매·용매 1

HCID 23444217Acetic acid tetrahydrofuran용매

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온도
0 °C

실험 절차

2-Amino-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide (Example Compound 35) (50 mg, 0.14 mmol) was dissolved in acetic acid/THF (1:1; 2 ml) and cooled to 0° C. Tert-butylnitrite (16.2 μl, 0.14 mmol) was added and the mixture was stirred for 1 h keeping the temperature between 0° C. -5° C. The reaction was quenched with water (3 ml), while keeping the temperature between 0° C. -5° C., and the organic phase was extracted with EtOAc (10 ml). The combined organic phases were washed with sat. sodium bicarbonate and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (11 mg, 23%)

후처리

  1. custombetween 0° C. -5° C
  2. customThe reaction was quenched with water (3 ml)
  3. custombetween 0° C. -5° C.
  4. extractionthe organic phase was extracted with EtOAc (10 ml)
  5. washThe combined organic phases were washed with sat. sodium bicarbonate
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with DCM as the eluent

출처 및 근거

ORD 기록
ord-ed881e856b9c45f9ad2f3bd945d6a6d8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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