Pyridine → N-[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-C-phenyl-methanesulfonamide

HRID 509985노트

반응식

HRID 509985 반응식
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[NH:12][CH:11]=1.N1C=CC=CC=1.[C:26]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[N:7]=[C:6]([NH:8][S:33]([CH2:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:35])=[O:34])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[NH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 582592126-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine

생성물 1

HCID 67200601N-[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-C-phenyl-methanesulfonamide수율 15.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

In a vial, 6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (137, 157 mg, 0.614 mmol) was mixed with 4 mL of dichloromethane and pyridine (149 μL, 1.84 mmol) and cooled to 0° C. in an ice water bath. Phenyl-methanesulfonyl chloride (139, 0.234 g, 1.23 mmol) was added and the reaction stirred at 0° C. for 1 hour, then warmed to room temperature and stirred overnight. Aqueous saturated sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 0-10% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (P-2181, 39 mg). MS (ESI) [M+H]+=411.1.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with 0-10% methanol in dichloromethane
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-9dae99e6517d477890a1fd3db0eca0b3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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