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Sodium hydride → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide

HRID 385874
ノート
印刷プレビュー

反応式

HRID 385874 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1.Cl[CH2:32][C:33]1[O:34][C:35]([CH3:38])=[N:36][N:37]=1>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[S:18][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][CH2:32][C:33]3[O:34][C:35]([CH3:38])=[N:36][N:37]=3)[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

生成物 1

HCID 595260635-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-[(6-{[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]methyl}pyridin-2-yl)amino]thiophene-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a suspension of NaH (14 mg, 0.35 mmol) in DMF (1.75 mL) at 0° C. under argon was added 5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 43) (70 mg, 0.17 mmol) and the mixture was allowed to stir for 10 minutes. 2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole (35 mg, 0.26 mmol) was then added and the reaction was allowed to warm to room temperature overnight. The reaction was then quenched by the addition of water, extracted with ethyl acetate and concentrated in vacuo. The crude residue was reverse phase HPLC (acteonitrile/water with formic acid as a modifier) to afford the title compound.

後処理

  1. customThe reaction was then quenched by the addition of water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b15539a6a0534b5fa6f23f9dedf8e208
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367706B2

反応ノート

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