Stannous Chloride → 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

HRID 384976Notes

Reaction equation

HRID 384976 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[O:20])[C:14]1=[O:28])([O-])=O.Cl[Sn]Cl>CCO>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH:8]2[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[O:20])[C:14]1=[O:28]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 498038661-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 498038671-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3.5 g, 1.0 eq) in EtOH (125 mL) was added SnCl2*2H2O (5.0 eq) in portions, the mixture was stirred at 70° C. overnight. At the end of reaction, the mixture was concentrated and ethyl acetate was added. The organic layer was washed with NaHCO3 aqueous for three times. The combined organic layer was washed with brine and dried over MgSO4, filtered and evaporated to give the crude product, which was purified by HPLC to afford 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3 g, 93%). MS (ESI) 347.0 (M+H); 1H NMR (300 MHz, DMSO-d6) δ12.44 (s, 1H), 8.49 (d, J=3.0 Hz, 2H), 8.46 (d, J=4.2 Hz, 1H), 7.72 (d, J=3.0 Hz, 2H), 7.57 (d, J=4.2 Hz, 1H), 6.96 (t, J=4.5 Hz, 1H), 6.57-6.61 (m, 2H), 6.45 (t, J=4.2 Hz, 1H), 6.31 (d, J=4.2 Hz, 1H), 5.19 (s, 2H), 2.85-2.90 (m, 1H), 2.65-2.75 (m, 2H), 2.00-2.05 (m, 1H).

Workup

  1. customAt the end of reaction
  2. concentrationthe mixture was concentrated
  3. additionethyl acetate was added
  4. washThe organic layer was washed with NaHCO3 aqueous for three times
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product, which
  10. customwas purified by HPLC

Sources & evidence

ORD record
ord-c30624537c7547a59ef53c9b4c4c2c19
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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