Potassium Carbonate → HCID 58168325, compound

HRID 1029275Notes

Reaction equation

HRID 1029275 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Br[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:1][CH2:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168325HCID 58168325, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 (172 mg, 0.81 mmol), methyl 4-(bromomethyl)benzoate (205 mg, 0.89 mmol), and K2CO3 (225 mg, 1.63 mmol) were suspended in DMF (3.00 mL), and stirred overnight at room temperature. The reaction mixture was purified directly via flash chromatography on silica gel to provide 454 (34 mg, 11% yield) as a white powder. LC-MS (M+H=360, obsd.=360). 1H NMR (400 MHz, DMSO-D6) δ 11.49 (s, 1H), 8.51 (m, 1H), 8.41 (d, J=3.0, 1H), 7.97 (dd, J=8.6, 19.3, 2H), 7.58 (d, J=8.2, 2H), 7.38 (m, 1H), 7.37 (s, 1H), 7.24 (dd, J=4.7, 7.9, 1H), 6.95 (d, J=11.0, 1H), 4.62 (s, 2H), 3.83 (s, 3H).

Workup

  1. customThe reaction mixture was purified directly via flash chromatography on silica gel

Sources & evidence

ORD record
ord-be39daf754f34de59bf8a975fff56e59
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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