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Sodium Bicarbonate → (4-Cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-4-hydroxymethyl-phenoxy)-pyridin-3-yl]-methanone

HRID 1025880
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HRID 1025880 반응식
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[C:18]([N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH:30]3[CH2:32][CH2:31]3)[CH2:22][CH2:21]2)=[O:19])=[CH:6][C:5]=1[Cl:33].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:30]1([N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:20]([C:18]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[O:11][C:7]3[CH:6]=[C:5]([Cl:33])[C:4]([CH2:3][OH:2])=[CH:9][C:8]=3[Cl:10])=[O:19])[CH2:21][CH2:22]2)[CH2:31][CH2:32]1
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 533121122,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester

생성물 1

HCID 53311273(4-Cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-[4-(2,5-dichloro-4-hydroxymethyl-phenoxy)-pyridin-3-yl]-methanone수율 26.6%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 0.10 g (0.20 mmol) 2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoic acid methyl ester (Example 27) in 1 mL tetrahydrofuran was added 0.008 g (0.21 mmol) lithium aluminium hydride. The resulting suspension was stirred at room temperature for 2.5 hours, poured on aqueous saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated to dryness. The resulting powder was purified by silica gel chromatography using a MPLC system (10 g silica gel column, CombiFlash Companion, Isco Inc.) with a gradient of n-heptane:ethyl acetate (100:0 to 50:50) to give 0.025 g (26%) of the desired compound as a light brown oil. MS (ESI): m/z=470.103 [M+H]+.

후처리

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated to dryness
  7. customThe resulting powder was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8cae39653460401f9e4b4b87ce9b9f18
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729091B2

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