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Dimethylformamide → N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride

HRID 655662
ノート
印刷プレビュー

反応式

HRID 655662 の反応式
[H-].[Na+].CN(C=O)C.[S:8]1[CH:12]=[CH:11][C:10]2[C:13]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]3)=[CH:14][CH:15]=[CH:16][C:9]1=2.[CH3:27][NH:28][C:29]([C:31]1[N:32]=[C:33]([Cl:36])[S:34][CH:35]=1)=[O:30]>O>[ClH:36].[CH3:27][NH:28][C:29]([C:31]1[N:32]=[C:33]([O:26][CH2:25][CH2:24][CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:13]3[C:10]4[CH:11]=[CH:12][S:8][C:9]=4[CH:16]=[CH:15][CH:14]=3)[CH2:22][CH2:21]2)[S:34][CH:35]=1)=[O:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 53630730N-methyl-2-chlorothiazole-4-carboxamideHCID 574825483-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propanol

生成物 1

HCID 66646049N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride収率 75.7%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
80 °C

実験手順

Sodium hydride (55%, oily, 90 mg, 2.2 mmol) was added to a DMF solution (2 ml) of 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propanol (0.2 g, 0.7 mmol) and N-methyl-2-chlorothiazole-4-carboxamide (0.26 g, 1.45 mmol) under ice cooling and the solution was stirred at 80° C. for 1.5 hours. After the reaction solution was cooled to room temperature and water was added thereto, it was extracted with ethyl acetate. The extraction solution with ethyl acetate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1→ethyl acetate). After the purified product was concentrated under reduced pressure, the residue was dissolved in ethyl acetate. A solution of 4N-hydrochloric acid/ethyl acetate was added to the solution and the insoluble matter precipitated was obtained by filtration and dried to obtain N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride (0.24 g) as light yellow powder.

後処理

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionit was extracted with ethyl acetate
  3. washThe extraction solution with ethyl acetate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=5:1→ethyl acetate)
  7. concentrationAfter the purified product was concentrated under reduced pressure
  8. dissolutionthe residue was dissolved in ethyl acetate
  9. additionA solution of 4N-hydrochloric acid/ethyl acetate was added to the solution
  10. customthe insoluble matter precipitated
  11. customwas obtained by filtration
  12. customdried

出典と根拠

ORDレコード
ord-55e31ec04b134923b524c7657c6c8526
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071600B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート