Water → ethyl 3-[3-phenyl-1-[2-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]propionate

HRID 350288ノート

反応式

HRID 350288 の反応式
[H-].[Na+].ClC[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[S:16][CH:17]=2)=[N:9][CH:10]=1.[C:24]1([C:30]2[C:34]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][NH:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.[CH3:43]N(C)C=O>>[C:24]1([C:30]2[C:34]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][N:32]([CH2:43][C:7]3[C:8]([O:11][CH2:12][C:13]4[N:14]=[C:15]([C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[S:16][CH:17]=4)=[N:9][CH:10]=[CH:5][CH:6]=3)[N:31]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 229307835-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridineHCID 178471160HCID 178471160、化合物

生成物 1

HCID 69421446ethyl 3-[3-phenyl-1-[2-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]propionate収率 74%

実験手順

Sodium hydride (60%, oily, 70.0 mg) was added to a solution of 5-chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine (554 mg), ethyl 3-(3-phenyl-1H-pyrazol-4-yl)propionate (428 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[3-phenyl-1-[2-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]propionate (678 mg, yield: 74%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 88–89° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-0b09ef9d978541c592269b625222b3e5
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

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