Sodium hydride → 1-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

HRID 1020212노트

반응식

HRID 1020212 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[C:14](=[CH:15][N:16]([CH3:22])[C:17](=[O:21])[C:18]=2[CH3:20])[NH:13]C1=O.[Si]([O:31][CH2:32][CH2:33][C:34]1([S:37](Cl)(=[O:39])=[O:38])[CH2:36][CH2:35]1)(C(C)(C)C)(C)C>CN(C=O)C.C1COCC1>[OH:31][CH2:32][CH2:33][C:34]1([S:37]([NH:13][C:14]2[C:19]([NH:11][C:5]3[CH:6]=[CH:7][C:8]([I:10])=[CH:9][C:4]=3[F:3])=[C:18]([CH3:20])[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=2)(=[O:39])=[O:38])[CH2:36][CH2:35]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 582598911-(2-fluoro-4-iodophenyl)-5,7-dimethyl-1H-imidazo[4,5-c]pyridine-2,6(3H,5H)-dioneHCID 593863261-[2-(Tert-butyldimethylsilanyloxy)ethyl]-cyclopropanesulfonyl chloride

생성물 1

HCID 589908331-(2-Hydroxyethyl)-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

NaH (60% in mineral oil) (21.8 mg, 0.544 mmol) is added to a solution of 1-(2-fluoro-4-iodophenyl)-5,7-dimethyl-1H-imidazo[4,5-c]pyridine-2,6(3H,5H)-dione (100 mg, 0.251 mmol) in dry DMF (5 mL) at 0° C. The cooling bath is removed and the solution stirred at room temperature for 1 hour. The solution is re-cooled to −5° C. in a dry-ice/acetone bath, and 1-[2-(tert-butyldimethylsilanyloxy)ethyl]-cyclopropanesulfonyl chloride (300 mg, 1 mmol) in dry THF (2 mL) is added. The mixture is warmed to room temperature and stirred for an additional 16 hours. The mixture is concentrated to give an oily residue and purified via flash chromatography (SiO2, EtOAc:MeOH=9:1) to give the title compound.

후처리

  1. customThe cooling bath is removed
  2. temperatureThe solution is re-cooled to −5° C. in a dry-ice/acetone bath
  3. temperatureThe mixture is warmed to room temperature
  4. stirringstirred for an additional 16 hours
  5. concentrationThe mixture is concentrated
  6. customto give an oily residue
  7. custompurified via flash chromatography (SiO2, EtOAc:MeOH=9:1)

출처 및 근거

ORD 기록
ord-a8019dead48c46728bd96663251883d4
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716318B2

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