1-Methylcyclopropanecarboxylic acid → Methyl 2-(1-methylcyclopropanecarbonyl)-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate

HRID 521423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521423
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Br.[O:26]=[C:27]1[C:36]2[CH2:35][CH2:34][NH:33][CH2:32][C:31]=2[NH:30][C:29]2[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([O:43][CH3:44])=[O:42])[C:28]1=2.[CH3:45][C:46]1([C:49](O)=[O:50])[CH2:48][CH2:47]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:45][C:46]1([C:49]([N:33]2[CH2:32][C:31]3[NH:30][C:29]4[CH:37]=[CH:38][CH:39]=[C:40]([C:41]([O:43][CH3:44])=[O:42])[C:28]=4[C:27](=[O:26])[C:36]=3[CH2:35][CH2:34]2)=[O:50])[CH2:48][CH2:47]1

Komponenten

6

Edukt 4

HCID 813261-Methylcyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89657238Methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate hydrobromide

Produkt 1

HCID 89657592Methyl 2-(1-methylcyclopropanecarbonyl)-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of HATU (340 mg, 0.9 mmol) in DMF (2 ml) was added to a mixture of methyl 5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (200 mg, 0.77 mmol) from Example 13 (Step 2), 1-methylcyclopropanecarboxylic acid (102 mg, 1.02 mmol), diisopropylethylamine (0.5 mL, 5.09 mmol) and DMF (8 ml). The resultant mixture was stirred at ambient temperature for 8 hours. The DMF was evaporated and the residue was purified by pre-TLC to give methyl 2-(1-methylcyclopropanecarbonyl)-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (65 mg, 25%) as yellow solid.

Aufarbeitung

  1. customThe DMF was evaporated
  2. customthe residue was purified by pre-TLC

Quellen und Nachweise

ORD-Eintrag
ord-9f890e39d41c4a4bb3e5b1589b744307
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328111B2

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