Sodium hydride → 3-([4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl](methyl)amino)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2222015

反応式

HRID 2222015 の反応式
[CH3:1][NH:2][C:3]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=1.[H-].[Na+].Cl[CH2:19][C:20]1[CH:38]=[CH:37][C:23]([O:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[O:33][CH:34]=[CH:35][CH:36]=3)[O:29][C:30]=2[CH3:31])=[C:22]([O:39][CH3:40])[CH:21]=1>CN(C)C=O>[O:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[C:28]1[O:29][C:30]([CH3:31])=[C:26]([CH2:25][O:24][C:23]2[CH:37]=[CH:38][C:20]([CH2:19][N:2]([CH3:1])[C:3]3[C:7]([CH:8]=[O:9])=[CH:6][N:5]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:4]=3)=[CH:21][C:22]=2[O:39][CH3:40])[N:27]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazoleHCID 230763643-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 866059253-([4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl](methyl)amino)-1-phenyl-1H-pyrazole-4-carbaldehyde収率 50.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde (150 mg) in N,N-dimethylformamide (5 mL) was added sodium hydride (60% in oil, 36 mg) on an ice bath, and the mixture was stirred for 30 min. To the reaction mixture was added 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-5-methyl-1,3-oxazole (227 mg), and the mixture was further stirred at room temperature for 1 hr. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to flash silica gel column chromatography and eluted with ethyl acetate-hexane (1:9 to 6:4, v/v) to give 3-([4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl](methyl)amino)-1-phenyl-1H-pyrazole-4-carbaldehyde as colorless crystals (170.4 mg, yield 46%). melting point: 101-102° C.

後処理

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-hexane (1:9 to 6:4, v/v)

出典と根拠

ORDレコード
ord-cc1af7221db54bea9531fe10f60e1f05
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

関連ノート

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