Dimethylamine → 5-{3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-pyridine-2-carboxylic acid dimethylamide

HRID 341458

Reaktionsgleichung

Reaktionsgleichung von HRID 341458
[CH3:1][NH:2][CH3:3].C[Al](C)C.C[Al](C)C.C1N2CCN(CC2)C1.C[O:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:34][N:33]=[C:32]([C:35]3[N:40]=[C:39]([NH2:41])[N:38]=[C:37]([N:42]([CH3:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:36]=3)[N:31]=2)=[CH:26][N:25]=1)=O>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][N:2]([CH3:3])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:34][N:33]=[C:32]([C:35]3[N:40]=[C:39]([NH2:41])[N:38]=[C:37]([N:42]([CH3:49])[C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)[N:36]=3)[N:31]=2)=[CH:26][N:25]=1)=[O:21]

Komponenten

6

Edukt 3

HCID 674DimethylamineHCID 166883661,4-Diazabicyclo(2.2.2)octane--trimethylalumane (1/2)HCID 66803428Methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate

Produkt 1

HCID 668027845-{3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-pyridine-2-carboxylic acid dimethylamideAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dimethylamine (248 μL, 0.495 mmol) and bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]-octane (128 mg, 0.495 mmol) were stirred together in anhydrous toluene (2 mL) at 40 C under nitrogen for 1 h. 5-{3-[4-Amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-pyridine-2-carboxylic acid methyl ester (prepared in an analogous manner to Example 279, 80 mg, 0.198 mmol) was added and the reaction stirred at 80 C for approximately 18 h. The mixture was then allowed to cool to room temperature and diluted with EtOAc (20 mL). The solution was then washed with 2M HCl (2×6 mL), saturated aq. sodium bicarbonate (2×6 mL), dried over sodium sulfate and evaporated under vacuum. The crude residue was purified by flash chromatography (0-3% MeOH in DCM) and the material obtained was then further purified by flash chromatography (0-80% EtOAc in heptane) to afford the title compound (10 mg, 12%).

Aufarbeitung

  1. additionwas added
  2. washThe solution was then washed with 2M HCl (2×6 mL), saturated aq. sodium bicarbonate (2×6 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude residue was purified by flash chromatography (0-3% MeOH in DCM)
  6. customthe material obtained
  7. customwas then further purified by flash chromatography (0-80% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-95549e403fbc43b3ac126b8ca8406567
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895733B2

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