Ethanesulfonyl chloride → HCID 178477688, 화합물

HRID 1888212노트

반응식

HRID 1888212 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C.[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]#[N:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:13]1[CH2:18][CH2:17][N:16]([S:30]([CH2:28][CH3:29])(=[O:32])=[O:31])[CH2:15][CH2:14]1

참가 물질

5

반응물 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178509434HCID 178509434, 화합물2회

생성물 1

HCID 178477688HCID 178477688, 화합물수율 42.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The crude 5-bromo-3-(4-piperidinyl)-1H-indazole-7-carbonitrile (Intermediate 9) (0.222 g, 0.493 mmol) was suspended in dichloromethane (5 mL) and treated with diisopropylethyl amine (0.257 mL, 1.48 mmols), and ethane sulfonyl chloride (0.070 mL, 0.74 mmols) at ambient temperature. After 2 hrs, the mixture was concentrated to dryness in vacuo at ambient temperature, treated with water (25 mL), and extracted with dichloromethane (100 mL). The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a light brown solid. This was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane) to give the title compound (0.083 g, 24%).

후처리

  1. concentrationthe mixture was concentrated to dryness in vacuo at ambient temperature
  2. additiontreated with water (25 mL)
  3. extractionextracted with dichloromethane (100 mL)
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light brown solid
  9. customThis was purified by combiflash (column 10 g, eluting with 100% dichloromethane, 5% ethyl acetate/dichloromethane, 30% ethyl acetate/dichloromethane)

출처 및 근거

ORD 기록
ord-eed87d0bc9cc4cb482088d501f566213
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501780B2

반응 노트

불러오는 중…