Triethylamine → 1-Methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide

HRID 553497ノート

反応式

HRID 553497 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.[CH3:26][N:27]1[CH:31]=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[N: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:32]([C:30]3[CH:29]=[N:28][N:27]([CH3:26])[CH:31]=3)(=[O:34])=[O:33])[CH2:18][CH2:17]2)=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 170247301-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 86640208{2-[4-(2-Chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amine hydrochloride salt

生成物 1

HCID 866402101-Methyl-1H-pyrazole-4-sulfonic acid {2-[4-(2-chloro-pyridin-3-yl)-piperazin-1-yl]-ethyl}-methyl-amide収率 66%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

Add triethylamine (3.403 mL, 24.414 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 (100 mL). Add 1-methyl-1H-pyrazole-4-sulfonyl chloride (1.102 g, 6.103 mmol) at room temperature. Stir at room temperature for 30 min. Dilute with dichloromethane and saturated aqueous sodium bicarbonate. Separate 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 (1.600 g, 66% yield). MS ES: m/z=399 [M+H]+.

後処理

  1. customat room temperature
  2. extractionSeparate phases and extract the aqueous phase with dichloromethane
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the resulting material by silica gel chromatography
  7. washeluting with hexanes:acetone 1:1
  8. customto afford the title
  9. custompreparation (1.600 g, 66% yield)

出典と根拠

ORDレコード
ord-fd7182ad77e7409db29493bbf1d6fd5c
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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