Sodium Hydroxide → n-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

HRID 351732ノート

反応式

HRID 351732 の反応式
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][Si](C)(C)C)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22714290n-Isopropyl-1-[3-(trimethylsilylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

生成物 1

HCID 9880627n-Isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The crude product from Step 1 was dissolved in methanol (12 mL/mmol) and 1N aqueous sodium hydroxide was added (3 eq), resulting in a suspension. The suspension mixture was stirred at room temperature for 2 hours and the methanol was evaporated. The resulting aqueous suspension was diluted with water and the product was extracted out with ethyl acetate. The crude product was chromatographed on silica gel eluting with 10% ether in methylene chloride to afford the N-isopropyl-1-(3-ethynylphenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide compound as a solid.

後処理

  1. customresulting in a suspension
  2. customthe methanol was evaporated
  3. additionThe resulting aqueous suspension was diluted with water
  4. extractionthe product was extracted out with ethyl acetate
  5. customThe crude product was chromatographed on silica gel eluting with 10% ether in methylene chloride

出典と根拠

ORDレコード
ord-269f20f8fa804628afc43a0d977e6a13
出典データセット
uspto-grants-2004_06
特許番号
US06743802B2

反応ノート

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