Sodium hydride → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-5-isopropyl-2-pyridinesulfonamide

HRID 1062739노트

반응식

HRID 1062739 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:29][CH2:30][CH2:31][OH:32])=[N:12][N:13]([CH3:28])[C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].[Br:35][C:36]1[CH:37]=[N:38][C:39](Cl)=[N:40][CH:41]=1>C1COCC1.CC(N(C)C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:29][CH2:30][CH2:31][O:32][C:39]4[N:40]=[CH:41][C:36]([Br:35])=[CH:37][N:38]=4)=[N:12][N:13]([CH3:28])[C:14]=3[NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 22281907HCID 22281907, 화합물

생성물 1

HCID 9895261N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-5-isopropyl-2-pyridinesulfonamide수율 24.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution of N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-5-isopropyl-2-pyridinesulfonamide (Example 43) (18 mg) in anhydrous THF (0.5 ml) at 0° C. and under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 3.3 mg) and the mixture was stirred for 5 minutes. To the mixture was added 5-bromo-2-chloropyrimidine (Liquid Crystals, 1993, 14(3), 741) (11.3 mg) in dimethylacetamide (0.1 ml). After stirring for 90 min, the reaction mixture was partitioned between ethyl acetate (3 ml) and saturated ammonium chloride solution (5 ml). The ethyl acetate layer was dried (MgSO4) and blown down under nitrogen to afford a gummy residue. Purification of the residue by column chromatography on silica gel (5 g), eluting in an isocratic fashion with ethyl acetate:hexane (7:4) afforded the title compound as a white solid (6 mg) after freeze drying from t-butanol.

후처리

  1. stirringAfter stirring for 90 min
  2. customthe reaction mixture was partitioned between ethyl acetate (3 ml) and saturated ammonium chloride solution (5 ml)
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. customto afford a gummy residue
  5. customPurification of the residue by column chromatography on silica gel (5 g)
  6. washeluting in an isocratic fashion with ethyl acetate:hexane (7:4)

출처 및 근거

ORD 기록
ord-3e3bc2f364944d03a659ca8a53b2da46
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

반응 노트

불러오는 중…