Sodium hydride → HCID 9829873、化合物

HRID 1062737ノート

反応式

HRID 1062737 の反応式
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:8]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][N:22]=2)(=[O:20])=[O:19])[N:7]([CH3:30])[N:6]=1.[H-].[Na+].Cl[C:34]1[N:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][N:35]=1>C1COCC1.CC(N(C)C)=O>[CH:27]([C:24]1[CH:25]=[CH:26][C:21]([S:18]([NH:17][C:8]2[N:7]([CH3:30])[N:6]=[C:5]([O:4][CH2:3][CH2:2][O:1][C:34]3[N:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][N:35]=3)[C:9]=2[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:19])=[O:20])=[N:22][CH:23]=1)([CH3:28])[CH3:29]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 156534822-Chloro-5-methanesulfonylpyrimidineHCID 22282040N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-5-isopropyl-2-pyridinesulfonamide

生成物 1

HCID 9829873HCID 9829873、化合物収率 20.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 31374Dimethylacetamide溶媒

実験手順

To a solution of N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-5-isopropyl-2-pyridinesulfonamide (Example 40) (112 mg) in anhydrous THF (5 ml) at 0° C. and under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 21.8 mg) and the mixture was stirred for 5 minutes. To the mixture was added 2-chloro-5-(methylsulfonyl)pyrimidine (50 mg) in dimethylacetamide (1 ml). After stirring for 150 min, the reaction mixture was partitioned between ethyl acetate (50 ml) and saturated ammonium chloride solution (50 ml). The ethyl acetate layer was washed with brine (50 ml), dried (MgSO4), filtered and evaporated to dryness. Purification of the residue on a Phenomenex Magellen™ column using a 0.1M NH4OAc:MeCN gradient (95;5 to 60:40) over 5 min. and then an isocratic flow (60:40) for 15 minutes gave the title compound as a white solid (31 mg).

後処理

  1. stirringAfter stirring for 150 min
  2. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and saturated ammonium chloride solution (50 ml)
  3. washThe ethyl acetate layer was washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification of the residue on a Phenomenex Magellen™ column
  8. waitMeCN gradient (95;5 to 60:40) over 5 min.

出典と根拠

ORDレコード
ord-35b5c06202d744829daaa4b19de2dc32
出典データセット
uspto-grants-2005_11
特許番号
US06962923B2

反応ノート

読み込み中…