1,2-Dimethoxyethane → 4-tert-Butyl-N-{3-[6-(4-formyl-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide

HRID 551870

Reaktionsgleichung

Reaktionsgleichung von HRID 551870
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[C:5](=[O:17])[N:4]([CH3:18])[CH:3]=1.[C:19]([C:23]1[CH:47]=[CH:46][C:26]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[C:31]=2[CH3:45])=[O:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].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>[C:19]([C:23]1[CH:47]=[CH:46][C:26]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=4)[C:5](=[O:17])[N:4]([CH3:18])[CH:3]=3)[C:31]=2[CH3:45])=[O:28])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 587289094-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehydeHCID 587289934-(tert-Butyl)-N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzamide

Produkt 1

HCID 587291394-tert-Butyl-N-{3-[6-(4-formyl-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamideAusbeute 111,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 4-(6-Bromo-4-methyl-3-oxo-3,4-dihydro-pyrazin-2-ylamino)-benzaldehyde (3) (2.0 g; 6.51 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (3.28 g; 7.8 mmol), tetrakis(triphenylphosphine)palladium (0.75 g; 0.65 mmol), 1N sodium carbonate (16.0 mL), and 1,2-dimethoxyethane (50 mL) was heated at 95° C. in a sealed pressure vessel for 12 hr. The mixture was cooled to room temperature, treated with water (70 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with water (2×75 mL) and brine (1×75 mL), dried over solid sodium sulfate, and evaporated under reduced pressure. The resulting residue was triturated with diethyl ether/dichloromethane to give 4-tert-butyl-N-{3-[6-(4-formyl-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-benzamide (4) as a light gray solid (3.6 g), MS 495.35 (M+H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with water (2×75 mL) and brine (1×75 mL)
  4. dry with materialdried over solid sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was triturated with diethyl ether/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7c49b10288d24be4bebc8187a002bc50
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947835B2

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