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2-Acetamido-4-chloromethylthiazole → N-(4-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-yl)acetamide

HRID 1252066
ノート
印刷プレビュー

反応式

HRID 1252066 の反応式
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]Cl)[N:9]=1)(=[O:3])[CH3:2].[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)[CH2:14][CH2:13]1.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:14][CH2:13]2)[N:9]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 819632-Acetamido-4-chloromethylthiazoleHCID 516892Sodium BicarbonateHCID 7022353-(4-Piperidinyl)-1H-indole

生成物 1

HCID 14129784N-(4-((4-(1H-Indol-3-yl)piperidin-1-yl)methyl)thiazol-2-yl)acetamide収率 30.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

2-Acetylamino-4-chloromethylthiazole (480 mg), 3-(4-piperidyl)indole (500 mg) and sodium hydrogen carbonate (310 mg) was refluxed in a mixture of N,N-dimethylformamide (5 ml) and tetrahydrofuran (7 ml) for 1 hour and 40 minutes. After the reaction mixture cooled to ambient temperature, it was concentrated under reduced pressure. After addition of water (50 ml), the residue was extracted with ethyl acetate (50 ml) twice. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and elution was carried out with a mixture of chloroform and methanol (30:1 V/V). The eluate gave 2-acetylamino-4-[4-(3-indolyl)piperidinomethyl]thiazole (270 mg).

後処理

  1. concentrationit was concentrated under reduced pressure
  2. additionAfter addition of water (50 ml)
  3. extractionthe residue was extracted with ethyl acetate (50 ml) twice
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was subjected to column chromatography on silica gel and elution
  8. additionwas carried out with a mixture of chloroform and methanol (30:1 V/V)

出典と根拠

ORDレコード
ord-2dbb26433cc1471a9e3144d3867d65c5
出典データセット
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04742057

反応ノート

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