Triethylamine → N-{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-4-fluoro-N-methyl-benzenesulfonamide

HRID 553496ノート

反応式

HRID 553496 の反応式
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH:24][CH3:25])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCl.C(=O)(O)[O-].[Na+]>[Cl:9][C:10]1[C:15]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:25])[S:33]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)(=[O:35])=[O:34])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 86640208{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt

生成物 1

HCID 86640209N-{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-4-fluoro-N-methyl-benzenesulfonamide収率 83%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

Add triethylamine (0.850 mL, 6.103 mmol) to a stirring solution of {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt (2.000 g, 6.103 mmol) in dichloromethane (10 mL). Stir at room temperature for 5 min. Add 4-fluoro-benzenesulfonyl chloride (0.356 g, 1.831 mmol) at room temperature. Stir at room temperature for 18 hr. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate the phases and extract the aqueous phase with dichloromethane. Combine the organic phases, dry over sodium sulfate, filter, and concentrate. Purify the resulting material by silica gel chromatography eluting with hexanes:acetone 1:1 to afford the title preparation (0.525 g, 83% yield). MS ES: m/z=413 [M+H]+.

後処理

  1. customat room temperature
  2. stirringStir at room temperature for 18 hr
  3. customSeparate the phases
  4. extractionextract the aqueous phase with dichloromethane
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the resulting material by silica gel chromatography
  9. washeluting with hexanes:acetone 1:1
  10. customto afford the title
  11. custompreparation (0.525 g, 83% yield)

出典と根拠

ORDレコード
ord-54539d651c06409fb3ad44fb1845c26f
出典データセット
uspto-grants-2011_11
特許番号
US08048884B2

反応ノート

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