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Hydrochloric Acid → (R)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411543
ノート
印刷プレビュー

反応式

HRID 2411543 の反応式
[CH3:1][S:2]([C:5]1[CH:15]=[C:14]([N:16]2[C@H:20]([CH3:21])[CH2:19][CH2:18][S:17]2(=[O:23])=[O:22])[CH:13]=[CH:12][C:6]=1[C:7](OCC)=[O:8])(=[O:4])=[O:3].[OH-].[Na+].Cl.Cl.[CH:28]1([C:31]2[CH:32]=[C:33]([CH3:43])[C:34]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[N:35][CH:36]=2)[CH2:30][CH2:29]1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(O)C.O>[CH:28]1([C:31]2[CH:32]=[C:33]([CH3:43])[C:34]([N:37]3[CH2:38][CH2:39][N:40]([C:7]([C:6]4[CH:12]=[CH:13][C:14]([N:16]5[C@H:20]([CH3:21])[CH2:19][CH2:18][S:17]5(=[O:23])=[O:22])=[CH:15][C:5]=4[S:2]([CH3:1])(=[O:3])=[O:4])=[O:8])[CH2:41][CH2:42]3)=[N:35][CH:36]=2)[CH2:30][CH2:29]1
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

9

反応物 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673810911-(5-Cyclopropyl-3-methylpyridin-2-yl)piperazine hydrochlorideHCID 71261164ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)benzoate

生成物 1

HCID 71252987(R)-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl][2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone収率 54.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Ethyl (R)-2-methanesulfonyl-4-(3-methyl-1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoate (361 mg) described in Preparation Example 28 was dissolved in ethanol (5 mL), 1N aqueous sodium hydroxide solution (1.5 mL) was added, and the mixture was stirred at 60° C. After completion of the reaction, the reaction mixture was neutralized with 1N hydrochloric acid (1.5 mL), 1-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine hydrochloride (254 mg) described in Preparation Example 82, N-methylmorpholine (0.2 mL) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (277 mg) were added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane) to give the title compound (292 mg).

後処理

  1. customAfter completion of the reaction
  2. additionwere added
  3. stirringthe mixture was stirred at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-898b43084ca44026a2ecc30ccff0a6e0
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08816079B2

反応ノート

読み込み中…

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