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(S)-(4-(3,4-Dichlorobenzyl)morpholin-2-YL)methanamine → n-{[(2s)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-2-[5-(4-fluorophenyl)-1,2,4oxadiazol-3-yl]acetamide

HRID 2212025
ノート
印刷プレビュー

反応式

HRID 2212025 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]([O:16]C)=O)[N:9]=2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:22][N:23]1[CH2:28][CH2:27][O:26][C@@H:25]([CH2:29][NH2:30])[CH2:24]1>CN1CCCC1=O.CO>[Cl:18][C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:22][N:23]1[CH2:28][CH2:27][O:26][C@@H:25]([CH2:29][NH:30][C:14](=[O:16])[CH2:13][C:10]2[N:9]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[O:12][N:11]=2)[CH2:24]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10171585(S)-(4-(3,4-Dichlorobenzyl)morpholin-2-YL)methanamineHCID 85817174Methyl (5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]acetate

生成物 1

HCID 68880198n-{[(2s)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-2-[5-(4-fluorophenyl)-1,2,4oxadiazol-3-yl]acetamide収率 57.4%

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone触媒HCID 887
Methanol
溶媒
2 回

実験手順

A mixture of Intermediate 38 (0.024 g), Intermediate 9 (0.025 g), and 1-methyl-2-pyrrolidinone (1 drop) was subjected was subjected to irradiation in a 600 W microwave oven on full power for 4 mins. The reaction mixture was dissolved in methanol and applied to an ion exchange cartridge (2 g Isolute SCX, pre-conditioned with methanol). Elution with methanol (3 column volumes) followed 10% 0.880 ammonia in methanol (2 column volumes) and evaporation of the first basic fraction in vacuo gave the crude product. Purification by Biotage flash column chromatography on silica gel (8 g cartridge), eluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia, gave the title compound as a white solid (0.025 g). LCMS (System A) Rf 2.85 min Mass Spectrum m/z 479, 481 [MH+]

後処理

  1. customwas subjected to irradiation in a 600 W microwave oven on full power for 4 mins
  2. washElution with methanol (3 column volumes)
  3. custom10% 0.880 ammonia in methanol (2 column volumes) and evaporation of the first basic fraction in vacuo
  4. customgave the crude product
  5. customPurification by Biotage flash column chromatography on silica gel (8 g cartridge)
  6. washeluting with 100:8:1 dichloromethane/ethanol/0.880 ammonia

出典と根拠

ORDレコード
ord-b7237dedf4304fe6a8fdb8ecdd4c9e3c
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07101882B2

反応ノート

読み込み中…

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