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Acetic Acid → (R)-2-(4-Chloro-2-methoxypyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69363
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HRID 69363 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH2:15][C@@H:16]([OH:19])[CH2:17][OH:18])[C:5]2=[O:20].CC(O)=O.[H][H].[Cl:27][C:28]1[C:33]([CH:34]=O)=[C:32]([O:36][CH3:37])[N:31]=[CH:30][CH:29]=1>CO.[Pd]>[Cl:27][C:28]1[CH:29]=[CH:30][N:31]=[C:32]([O:36][CH3:37])[C:33]=1[C:34]1[NH:11][C:10]2=[CH:9][C:8]3[C:7](=[O:14])[N:6]([CH2:15][C@@H:16]([OH:19])[CH2:17][OH:18])[C:5](=[O:20])[C:4]=3[CH:3]=[C:2]2[N:1]=1
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7

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HCID 176Acetic Acid2회HCID 534079284-Chloro-2-methoxypyridine-3-carbaldehydeHCID 66686469(R)-5-Amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dioneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 66687275(R)-2-(4-Chloro-2-methoxypyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione수율 29.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매2회

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온도
-30 °C

실험 절차

To a suspension of (R)-5-amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dione (0.50 g, 1.78 mmol) in 100 mL of MeOH was added 5 mL of AcOH. The resulting solution was degassed with Argon and then charged with 10% Pd/C (0.19 g, 50% wet, 0.089 mmol) and hydrogenated at 40 psi of hydrogen for 16 h. Another 5 mL of AcOH was added to the mixture and then solids were filtered off. The filtrate was cooled to −30° C. and a solution of 4-chloro-2-methoxynicotinaldehyde (0.31 g, 1.78 mmol) in 50 mL of MeOH was added dropwise under inert atmosphere. The resulting red clear solution was allowed to warm up to rt and stirred for 16 h. Solvent was evaporated and the oily residue was purified by column chromatography (7.5% MeOH in dichloromethane) to give title compound as a yellow solid (0.21 g, 29.3%). 1H NMR (500 MHz, DMSO-d6) δ 8.37 (d, J=5.5 Hz, 1H), 8.07 (s, 2H), 7.40 (d, J=5.5 Hz, 1H), 4.92 (d, J=5.0 Hz, 1H), 4.67 (br s, 1H), 4.20-4.14 (br s, 1H), 3.90 (s, 3H), 3.90-3.80 (m, 1H), 3.64-3.60 (m, 2H), 3.42-3.36 (m, 2H). ESI MS: m/z 403.1 (M+1).

후처리

  1. customThe resulting solution was degassed with Argon
  2. filtrationsolids were filtered off
  3. temperatureto warm up to rt
  4. customSolvent was evaporated
  5. customthe oily residue was purified by column chromatography (7.5% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-cefd83594b3949d4815d9b1124091d56
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822500B2

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