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

HRID 1039616노트

반응식

HRID 1039616 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-48bcf51177aa4005a0190a4cb49f0827
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552193B2

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