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

HRID 513599ノート

反応式

HRID 513599 の反応式
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

参加物

4

反応物 2

HCID 10906Tert-Butyl nitriteHCID 167595482-Amino-N-quinolin-8-yl-4-trifluoromethyl-benzenesulfonamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 23444217Acetic acid tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-ed881e856b9c45f9ad2f3bd945d6a6d8
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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