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

HRID 385873ノート

反応式

HRID 385873 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.Br[CH2:32][CH2:33][O:34][CH3:35]>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][CH2:33][O:34][CH3:35])[N:21]=2)=[C:16]([C:28]([NH2:30])=[O:29])[CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 251234855-(2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl)-2-((6-(hydroxymethyl)-2-pyridinyl)amino)-3-thiophenecarboxamide

生成物 1

HCID 595257925-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-[(2-methoxyethoxy) methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of NaH (7.5 mg, 0.19 mmol) in DMF (1.25 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) (50 mg, 0.13 mmol) and the mixture was allowed to stir for 10 minutes. 1-Bromo-2-methoxyethane (26 mg, 0.187 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-92db7a6066574ad2989834fe3ccc069d
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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