Potassium Cyanide → 1-(4-cyano-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

HRID 384977Notes

Reaction equation

HRID 384977 reaction equation
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:18])[C:12]1=[O:26].N([O-])=O.[Na+].[C:31]([Cu])#[N:32].[C-]#N.[K+]>O.Cl>[C:31]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:18])[C:12]1=[O:26])#[N:32]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 23668193Sodium NitriteHCID 498038671-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideHCID 178418546HCID 178418546, compound

Product 1

HCID 498038681-(4-cyano-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamideYield 10%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

To a mixture of 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (200 mg, 1.0 eq) in H2O (4 mL) and conc. HCl (0.5 mL) was dropped the materials of NaNO2 (1.1 eq) in 1 mL of H2O at 0° C., the mixture was stirred at room temperature for 30 minutes. Then this mixture was added to another flask contained CuCN (9.0 eq), KCN (8.8 eq) and 2 mL H2O at 0° C., maintained stiffing for 5 h. At the end of reaction, FeSO4 aqueous was added to the mixture, filtrated and washed the solid substance with DMSO, evaporated the filtrate to give the crude product, which was purified by HPLC to afford 1-(4-cyano-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (20 mg, 10%). MS (ESI) 357.0 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.48 (br, 1H), 8.47 (d, J=4.5 Hz, 2H), 7.83 (d, J=4.5 Hz, 1H), 7.79 (bd, 1H), 7.72 (bs, 2H), 7.52 (d, J=4.5 Hz, 1H), 7.45 (t, J=4.5 Hz, 1H), 6.61 (m, 2H), 3.3 (overlap with DMSO-d6, 1H), 3.10-3.25 (m, 1H), 2.70-2.80 (m, 1H), 2.20-2.27 (m, 1H).

Workup

  1. additionThen this mixture was added to another flask
  2. customat 0° C.
  3. temperaturemaintained
  4. waitstiffing for 5 h
  5. additionwas added to the mixture
  6. filtrationfiltrated
  7. washwashed the solid substance with DMSO
  8. customevaporated the filtrate
  9. customto give the crude product, which
  10. customwas purified by HPLC

Sources & evidence

ORD record
ord-92921f0b9606483c9e5603b24af58420
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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