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(2-Methoxyethyl)(methyl)amine → (E)-N-(2-Methoxyethyl)-N-methyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide

HRID 2075433
ノート
印刷プレビュー

反応式

HRID 2075433 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)=[N:2]1.[CH3:21][O:22][CH2:23][CH2:24][NH:25][CH3:26].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C1COCC1>[CH3:21][O:22][CH2:23][CH2:24][N:25]([CH3:26])[C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12](/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid

生成物 1

HCID 67089879
(E)-N-(2-Methoxyethyl)-N-methyl-4-[2-(1H-indazol-3-yl)vinyl]benzamide
収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (0.18 g, 0.67 mmol) obtained in Step 6 of Example 1 was dissolved in THF (4 mL), and the solution was added with N-(2-methoxyethyl)methylamine (0.11 mL, 1.00 mmol), 1-hydroxybenzotriazole monohydrate (0.12 g, 0.85 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.18 g, 0.92 mmol), followed by stirring at room temperature for 2 hours. The reaction mixture was added with a saturated aqueous sodium hydrogencarbonate solution, was extracted with ethyl acetate, the organic layer was sequentially washed with water and saturated brine, was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=25/1) to obtain Compound 5 (0.22 g, 99%).

後処理

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was sequentially washed with water and saturated brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=25/1)

出典と根拠

ORDレコード
ord-9e731d97d5ce451d8cd6eb768042fdeb
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07919517B2

反応ノート

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