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 1368598ノート

反応式

HRID 1368598 の反応式
[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

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 156534822-Chloro-5-methanesulfonylpyrimidineHCID 22281907HCID 22281907、化合物

生成物 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-pyridinesulfonamide収率 13.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4915e37e9a354fc79efd8e5b8c77fb71
出典データセット
uspto-grants-2003_06
特許番号
US06573270B1

反応ノート

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