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Benzamide → N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

HRID 68658
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 68658
CNCCNC.I[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH:26]([CH3:28])[CH3:27])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[N:15]=2)[N:10]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:9]=1.[C:39]([NH2:47])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH:26]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:15]=[C:16]3[C:8]([NH:47][C:39](=[O:46])[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:9][N:10]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:11]3=[N:12][CH:13]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25])([CH3:27])[CH3:28]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 2331BenzamideHCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 667631397-Iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 71143663N-(2-(4-(isopropylsulfonyl)phenyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)benzamideAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

CuI (95 mg, 0.4988 mmol), and N,N′-dimethylethane-1,2-diamine (176 mg, 1.997 mmol) in dioxane (5 mL) was heated for 5 minutes at 100° C. in a microwave. 1 mL of this solution was added to a mixture of 7-iodo-2-(4-isopropylsulfonylphenyl)-5-(p-tolylsulfonyl)pyrrolo[2,3-b]pyrazine (100 mg, 0.1720 mmol), benzamide (104.2 mg, 0.8600 mmol) and K3PO4 (73.02 mg, 0.344 mmol) in dioxane (1 mL) and the solution was heated at 95° C. for 1 hour. The reaction mixture is concentrated in vacuo. The residue was partitioned between DCM and water. Combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo yielding an oil which was purified by prep HPLC to give the sub-title product (37 mg, 37%). MS (ES+) 575.1.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding an oil which
  7. customwas purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c9d1960d0ea24e88ab301818a7fa4b81
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822469B2

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