Triethylamine → 1-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone

HRID 2388697ノート

反応式

HRID 2388697 の反応式
[N:1]1([C:6]2[CH2:11][CH2:10][N:9]([C:12](=[O:14])[CH3:13])[CH2:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:15]/[N:16]=[C:17](\Cl)/[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[N:21]1[CH:22]=[CH:23][C:18]([C:17]2[CH:7]3[CH2:8][N:9]([C:12](=[O:14])[CH3:13])[CH2:10][CH2:11][C:6]3([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[O:15][N:16]=2)=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 141055951-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanoneHCID 135723912N-hydroxypyridine-4-carbonimidoyl chloride

生成物 1

HCID 686439771-(3-(Pyridin-4-yl)-7a-(pyrrolidin-1-yl)-3a,4,7,7a-tetrahydroisoxazolo[4,5-c]pyridin-5(6H)-yl)ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

反応条件

温度
0 °C

実験手順

1-(4-(Pyrrolidin-1-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (1.2 g, 6.176 mmol) (synthesis: see below) was dissolved in methylene chloride (10 ml) and the solution was cooled to 0° C. under an inert gas. (Z)-N-Hydroxyisonicotinimidoyl chloride (1.45 g, 9.264 mmol), dissolved in methylene chloride (5 ml), and triethyl-amine (2.1 ml, 14.82 mmol), dissolved in methylene chloride (5 ml), were added, stir for 15 h, during this allow to warm to room temperature. The mixture was diluted with methylene chloride (30 ml) and washed water (20 ml) and citric acid (10%, 20 ml). The aqueous phase was neutralized with sodium bicarbonate and extracted with methylene chloride and the combined organic phases were washed with saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25% eq.) 100/10/1. The yield was 0.64 g (33%).

後処理

  1. additionwere added
  2. temperatureto warm to room temperature
  3. washwashed water (20 ml) and citric acid (10%, 20 ml)
  4. extractionextracted with methylene chloride
  5. washthe combined organic phases were washed with saturated sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel) with ethyl acetate/methanol/ammonia (25% eq.) 100/10/1

出典と根拠

ORDレコード
ord-4f23282ce97e4e13bf21d57d10b8082e
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

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