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

HRID 1062740노트

반응식

HRID 1062740 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+].Cl[C:36]1[N:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][N:37]=1>C1COCC1.CC(N(C)C)=O>[C:31]([O-:32])(=[O:43])[CH3:30].[NH4+:12].[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:36]4[N:41]=[CH:40][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][N:37]=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

7

반응물 3

HCID 24758Sodium hydrideHCID 156534822-Chloro-5-methanesulfonylpyrimidineHCID 22281907HCID 22281907, 화합물

생성물 2

HCID 517165Ammonium AcetateHCID 9809165N-[4-(1,3-benzodioxol-5-yl)-1-methyl-3-(2-{[5-(methylsulfonyl)-2-pyrimidinyl]oxy}ethoxy)-1H-pyrazol-5-yl]-5-isopropyl-2-pyridinesulfonamide수율 13.2%

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) (124 mg) in anhydrous THF (5 ml) at 0° C. and under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 33.9 mg) and the mixture was stirred for 5 minutes. To the mixture was added 2-chloro-5-(methylsulfonyl)pyrimidine (93 mg) in dimethylacetamide (1 ml). After being left to stir overnight, the reaction mixture was partitioned between ethyl acetate (100 ml) and saturated ammonium chloride solution (100 ml). The ethyl acetate layer was washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated to dryness. Purification of the residue on a Phenomenex Magellen™ column eluting in an isocratic fashion with acetonitrile:ammonium acetate solution (0.1M) (3:7) afforded the title compound as a white solid (11 mg).

후처리

  1. waitAfter being left
  2. stirringto stir overnight
  3. customthe reaction mixture was partitioned between ethyl acetate (100 ml) and saturated ammonium chloride solution (100 ml)
  4. washThe ethyl acetate layer was washed with brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customPurification of the residue on a Phenomenex Magellen™ column
  9. washeluting in an isocratic fashion with acetonitrile

출처 및 근거

ORD 기록
ord-fb041dc2807b40abbb06608c095f8380
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962923B2

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