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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
ノート
印刷プレビュー

反応式

HRID 69363 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic Acid2 回HCID 534079284-Chloro-2-methoxypyridine-3-carbaldehydeHCID 66686469(R)-5-Amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dioneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒

2
HCID 23938Palladium触媒HCID 887Methanol溶媒2 回

反応条件

温度
-30 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cefd83594b3949d4815d9b1124091d56
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822500B2

反応ノート

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