Pyridine → 6,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate

HRID 917370노트

반응식

HRID 917370 반응식
N1C=CC=CC=1.[NH2:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>Cl>[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([NH:7][C:8]2[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 230203546,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

생성물 1

HCID 230202826,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate수율 90.1%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

To 5 ml of pyridine was dissolved 0.62 g (2.3 mmol) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate, followed by the addition of 0.48 g (2.5 mmol) of toluene-4-sulfonylchloride under ice-cooling, stirring for 10 minutes and then stirring at room temperature for 15 hours. The reaction liquid was then poured in 5% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 0.88 g (yield: 90%) of 6,6-difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate.

후처리

  1. temperaturecooling
  2. stirringstirring at room temperature for 15 hours
  3. customThe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2)

출처 및 근거

ORD 기록
ord-d9945211f11440aca5ad09f2c632ea28
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273878B2

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