HCID 22252596, compound → HCID 22252599, compound

HRID 1612040Notes

Reaction equation

HRID 1612040 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:30][CH3:31])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]4[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][C:12]4=[N:13][CH:14]=3)[N:9]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:8](=[O:28])[C:7]=2[CH:29]=1>C(O)C.[Ni].O.NN>[NH2:20][C:19]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]3[C:10]=2[N:9]([CH2:23][CH2:24][N:25]([CH3:26])[CH3:27])[C:8](=[O:28])[C:7]2[CH:29]=[C:3]([O:2][CH3:1])[C:4]([O:30][CH3:31])=[CH:5][C:6]3=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 22252596HCID 22252596, compound

Product 1

HCID 22252599HCID 22252599, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 24654Hydrazine hydrate (1:1)CatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of compound 3d (37 mg, 0.088 mmol) in ethanol (8 mL) was added 1 pinch of Raney Nickel and 5 drops of hydrazine hydrate, and the mixture was stirred at ambient temperature for 2 h. The mixture was filtered through Celite and the filtrate was evaporated. The residue was dissolved in chloroform (25 mL) and washed with brine (25 mL), dried (MgSO4), and evaporated, giving 28 mg (81%) as a yellow solid; mp 239-241° C.; 1H NMR (CDCl3) δ 1.80 (s, 6H), 2.10 (m, 2H), 4.05 (s, 3H), 4.13 (s, 3H), 4.48 (m, 3H), 5.07 (m, 1H), 6.79 (dd, 1H, J=6.3, J=2.5), 7.52 (m, 2H), 7.64 (s, 1H), 7.87 (s, 1H), 9.38 (s, 1H); 13C NMR (CDCl3) δ 45.1, 50.5, 56.3, 56.4, 57.4, 102.0, 109.1, 109.6, 111.3, 112.6, 118.7, 119.5, 127.7, 130.0, 141.0, 142.6, 144.8, 149.8, 150.0, 154.3, 164.5; HRMS calcd for C22H24O3N4H: 393.1927; found: 393.1925.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in chloroform (25 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customgiving 28 mg (81%) as a yellow solid

Sources & evidence

ORD record
ord-60d3620867c84b5ab3cf79522cf44980
Source dataset
uspto-grants-2006_01
Patent number
US06992089B2

Reaction notes

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