Triethylamine → (2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methyl-4-(2-pyridinylcarbonyl)piperazine hydrochloride

HRID 41310

反応式

HRID 41310 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]2[CH3:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32](Cl)=[O:33]>C(Cl)Cl>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)=[O:33])[CH2:14][C@@H:13]2[CH3:18])(=[O:10])=[O:11])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 67028562(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride

生成物 1

HCID 44611965(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methyl-4-(2-pyridinylcarbonyl)piperazine hydrochloride収率 72.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2S)-1-[(4-chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride (Description 4) (200 mg, 0.728 mmol) in DCM (8 mL) was added triethylamine (0.172 ml, 1.237 mmol) and the reaction was cooled to 0° C. and stirred under argon. 2-pyridinecarbonyl chloride (155 mg, 0.873 mmol) was added portionwise and the reaction was slowly allowed to warm to rt, stirring continued for 18 hours. The sample was evaporated, the crude residue was purified by silica chromatography (5 g silica SPE), (eluting a gradient from 20-90% ethyl acetate in hexane) and the product containing fractions were concentrated. The product was then dissolved in 1,4-dioxane (2 ml) to this was added 1M ethereal HCl (4 ml) the sample was evaporated and then triturated in diethyl ether until solid. The solid was dried under vacuum at 40° C. for 18 hours to yield the title compound as a white solid (110 mg)

後処理

  1. temperatureto warm to rt
  2. stirringstirring
  3. customThe sample was evaporated
  4. customthe crude residue was purified by silica chromatography (5 g silica SPE)
  5. wash(eluting a gradient from 20-90% ethyl acetate in hexane) and the product
  6. additioncontaining fractions
  7. concentrationwere concentrated
  8. dissolutionThe product was then dissolved in 1,4-dioxane (2 ml) to
  9. additionthis was added 1M ethereal HCl (4 ml) the sample
  10. customwas evaporated
  11. customtriturated in diethyl ether until solid
  12. customThe solid was dried under vacuum at 40° C. for 18 hours

出典と根拠

ORDレコード
ord-552fa5a9373a423c9da8dad1d5e7a757
出典データセット
uspto-grants-2013_09
特許番号
US08530478B2

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