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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Piperidine → (S,Z)-N-{5-fluoro-3-[5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-2-hydroxy-acetamide

HRID 2068735
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HRID 2068735 반응식
[OH:1][C@@H:2]([CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]2[NH:10][C:11]([CH:14]=O)=[C:12]([CH3:13])[C:6]=2[C:5]1=[O:16].[F:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[NH:34][C:35](=[O:38])[CH2:36][OH:37])[NH:30][C:29](=[O:39])[CH2:28]2.N1CCCCC1>C(O)C>[F:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:33]=1[NH:34][C:35](=[O:38])[CH2:36][OH:37])[NH:30][C:29](=[O:39])/[C:28]/2=[CH:14]\[C:11]1[NH:10][C:7]2[CH2:8][CH2:9][N:4]([CH2:3][C@@H:2]([OH:1])[CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:5](=[O:16])[C:6]=2[C:12]=1[CH3:13]
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참가 물질

5

반응물 3

HCID 8082PiperidineHCID 45118149N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxyacetamideHCID 59375986(S)-5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

생성물 1

HCID 25207649(S,Z)-N-{5-fluoro-3-[5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-2-hydroxy-acetamide수율 86.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1 H-pyrrolo[3,2-c]pyridine-2-carbaldehyde 5f (40 mg, 0.125 mmol) was dissolved in 2 mL of ethanol under stirring at room temperature, and N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-acetamide 9f (25.1 mg, 0.112 mmol) was then added to the solution. Upon completion of the addition, the mixture was stirred until all dissolved, and piperidine (50 μL, 0.5 mmol) was then added to the reaction solution. Upon completion of the addition, the reaction system was stirred at 80° C. in an oil bath in dark for 2 hours. The reaction was completed until TLC showed the disappearance of starting materials, and the oil bath was removed. The reaction system was naturally cooled down to room temperature to precipitate solids. The resulting solids were filtered to give the title compound (S,Z)-N-{5-fluoro-3-[5-(2-hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-2-hydroxy-acetamide 9 (51 mg, yield 80%) as a yellow solid.

후처리

  1. additionUpon completion of the addition
  2. additionwas then added to the reaction solution
  3. additionUpon completion of the addition
  4. stirringthe reaction system was stirred at 80° C. in an oil bath in dark for 2 hours
  5. customthe oil bath was removed
  6. temperatureThe reaction system was naturally cooled down to room temperature
  7. customto precipitate solids
  8. filtrationThe resulting solids were filtered

출처 및 근거

ORD 기록
ord-15072c2c61414aef8e4ff904cd1486cc
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299069B2

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