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3-Bromopentane → 4-(4-oxo-1-(pentan-3-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206147
ノート
印刷プレビュー

反応式

HRID 2206147 の反応式
[O:1]=[C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[S:14][CH:15]=3)=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][NH:3]1.[H-].[Na+].Br[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24]>CN(C=O)C>[O:1]=[C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[S:14][CH:15]=3)=[N:9][N:10]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:6]=2[CH:5]=[CH:4][NH:3]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 157383-BromopentaneHCID 24758Sodium hydrideHCID 1370107094-(4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

生成物 1

HCID 1370107104-(4-oxo-1-(pentan-3-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (80.0 mg) obtained in Step A of Example 141 in DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil, 24.6 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 3-bromopentane (93.0 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol) to give the title compound (51.8 mg).

後処理

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-2e21c1edf9364beead7657f750f3f96b
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09371320B2

反応ノート

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