홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Lithium hydroxide, monohydrate → 4-Oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid

HRID 1497697
노트
인쇄 미리보기

반응식

HRID 1497697 반응식
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:4]=[C:3]1[C:29]([O:31]CC)=[O:30].O.[OH-].[Li+]>CS(C)=O.CO.O.C(#N)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:4]=[C:3]1[C:29]([OH:31])=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725449Ethyl 4-oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylate

생성물 1

HCID 769026754-Oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid수율 43.2%

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide용매
HCID 887
Methanol
용매
HCID 962Water용매2회
HCID 6342Acetonitrile용매

실험 절차

To a solution of ethyl 4-oxo-1-((4′-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylate (37) (11 mg, 0.024 mmol) in dimethyl sulfoxide (1 mL) and methanol (5 mL) was added the solid lithium hydroxide monohydrate (51.0 mg, 1.22 mmol) at room temperature under a nitrogen atmosphere. It gave a clear solution within 30 minutes and this light yellow solution was stirred for 15 h at which time LCMS analysis indicated the absence of starting material. Then, the mixture was diluted with water and the methanol was removed under vacuum. The basic aqueous layer was diluted with water and then neutralized with 1.0N HCl. The resulting acid was extracted with ethyl acetate (2×30 mL) and the combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave a brown residue which was dissolved in acetonitrile and water. It was frozen and then lyophilized under high vacuum to obtain 4-oxo-1-((4′-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (38) (4.4 mg, 42.6% yield) as a light yellow solid.

후처리

  1. customIt gave a clear solution within 30 minutes
  2. customthe methanol was removed under vacuum
  3. additionThe basic aqueous layer was diluted with water
  4. extractionThe resulting acid was extracted with ethyl acetate (2×30 mL)
  5. washthe combined extracts were washed with brine solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltration and concentration
  8. customgave a brown residue which
  9. temperatureIt was frozen

출처 및 근거

ORD 기록
ord-26ff61e305004141b2d466ea1a72fd96
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199987B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트