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Ethanolamine → 5-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide

HRID 1641737
ノート
印刷プレビュー

反応式

HRID 1641737 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16](O)=[O:17])=[N:14][CH:15]=2)=[CH:4][CH:3]=1.[NH2:29][CH2:30][CH2:31][OH:32].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]([C:20]2[C:25]([F:26])=[CH:24][CH:23]=[C:22]([F:27])[C:21]=2[F:28])[C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:29][CH2:30][CH2:31][OH:32])=[O:17])=[N:14][CH:15]=2)=[CH:4][CH:3]=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 700EthanolamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577364725-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxylic Acid

生成物 1

HCID 57736478
5-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide
収率 97.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-[[(4-fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-m ethylpyridine-2-carboxylic acid (163 mg, 0.40 mmol) obtained in Example 34 in methylene chloride (5 ml), 2-aminoethanol (0.027 ml, 0.44 mmol), 1-hydroxybenzotriazole (60 mg, 0.44 mmol), 4-methylmorpholine (0.048 ml, 0.44 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (84 mg, 0.44 mmol) were added at room temperature. After stirring for 3 hours at room temperature, the reaction mixture was washed with water and then with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=2:3 was concentrated under reduced pressure to obtain the title compound (175 mg, 0.39 mmol, 97%) as a colorless oily substance.

後処理

  1. washthe reaction mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=2:3 was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-70d3a316d16f492db24b2072dd0413cb
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114886B2

反応ノート

読み込み中…

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