1,4-Dioxane → n-Acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide

HRID 2193019Notes

Reaction equation

HRID 2193019 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:15]([CH3:17])[CH3:16])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[H+].[B-](F)(F)(F)F.[O:39]1[CH2:44][CH2:43]OCC1.C([N:48](CC)C(C)C)(C)C.C[C:55]([N:57](C)C)=[O:56]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[C:44]([N:57]([C:55]([C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:15]([CH3:17])[CH3:16])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1)=[O:56])[NH2:48])(=[O:39])[CH3:43]

Participants

8

Reactant 5

HCID 312751,4-DioxaneHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 593756889-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-oneHCID 86626500tri-(t-butyl)phosphonium HBF4

Product 1

HCID 67415394n-Acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
100 °C

Procedure

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (100 mg, 0.32 mmol), acetichydrazide (47 mg, 0.63 mmol), molybdenum hexacarbonyl (83 mg, 0.32 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (15 mg, 0.016 mmol), and tri-(t-butyl)phosphonium HBF4 salt (9.2 mg, 0.032 mmol) were combined in a vial, followed by dioxane (2.0 ml), DMA (1.0 ml) and N,N-diisopropylethylamine (0.22 ml, 1.3 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, and then stirred at 100° C. in a sealed vial for 3 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (3 mL), and filtered to afford N-acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide. 1H NMR (500 MHz, DMSO-D6) δ 11.88 (d, 1H), 10.53 (s, 1H), 10.47 (d, 1H), 9.97 (s, 1H), 8.56 (d, 1H), 8.06 (dd, 1H), 7.57 (t, 1H), 6.79 (d, 1H), 4.12 (septet, 1H), 1.94 (s, 3H), 1.38 (d, 6H). LRMS (ESI) calc'd for (C18H18N4O3) [M+H]+, 339.1; found 339.1.

Workup

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with EtOAc (3 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-245186ffe5bd40a083292f3e08767dcf
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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