1,2-Dimethoxyethane → 4-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid ethyl ester

HRID 551854

Reaktionsgleichung

Reaktionsgleichung von HRID 551854
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14](Br)[N:13]=2)=[CH:7][CH:6]=1)[CH3:2].[C:22]([C:26]1[CH:50]=[CH:49][C:29]([C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35](B3OC(C)(C)C(C)(C)O3)[C:34]=2[CH3:48])=[O:31])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14]([C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([NH:32][C:30](=[O:31])[C:29]4[CH:28]=[CH:27][C:26]([C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:50][CH:49]=4)[C:34]=3[CH3:48])[N:13]=2)=[CH:7][CH:6]=1)[CH3:2]

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 58728992HCID 58728992, VerbindungHCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Produkt 1

HCID 118525664-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid ethyl esterAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-(6-bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzoic acid ethyl ester (2) (340 mg; 0.97 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (5) (457 mg; 1.16 mmol), tetrakis(triphenylphosphine)palladium (56 mg; 0.05 mmol), 1N sodium carbonate (2.9 mL; 2.9 mmol), and 1,2-dimethoxyethane (30 mL) was heated at 100 degrees in a sealed pressure vessel for 16 hr. The mixture was cooled to room temperature, treated with water (70 mL) and extracted with ethyl acetate (3×60 mL). The combined organic extracts were washed with water (2×40 mL) and brine (1×40 mL), dried over magnesium sulfate, and evaporated under reduced pressure. The resulting residue was triturated with diethyl ether/dichloromethane to give 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino}-benzoic acid ethyl ester (6) as a gray solid (330 mg), MS 539.49 (M+H).

Aufarbeitung

  1. temperaturewas heated at 100 degrees in a sealed pressure vessel for 16 hr
  2. extractionextracted with ethyl acetate (3×60 mL)
  3. washThe combined organic extracts were washed with water (2×40 mL) and brine (1×40 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was triturated with diethyl ether/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-81ee4818619f4b709032a81413487f9c
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947835B2

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