Triethylamine → HCID 178477691, 화합물

HRID 1888215노트

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HRID 1888215 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:15][CH2:16][N:17]([S:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH2:18][CH2:19]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 178513507HCID 178513507, 화합물2회

생성물 1

HCID 178477691HCID 178477691, 화합물수율 32%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The crude 5-bromo-3-(4-piperidinyl)-1H-indazole-7-carboxamide (Intermediate 6) (1.23 mmol) was suspended in dichloromethane (20 mL) and treated with triethyl amine (0.856 mL, 6.15 mmols), and ethane sulfonyl chloride (0.175 mL, 1.85 mmols) at 0° C. 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 (0.161 g, 32%).

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-0081fca7190c4de389e3dac092b153f7
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501780B2

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