HCID 178478839, compound → HCID 69903148, compound

HRID 357617Notes

Reaction equation

HRID 357617 reaction equation
[ClH:1].Cl.O[NH:4][C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[C:20]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[N:19]=[C:18]1[NH2:32])=[NH:6]>[Ni].CO.O>[ClH:1].[ClH:1].[C:5]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[N:16][N:17]1[CH:21]=[C:20]([C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[N:19]=[C:18]1[NH2:32])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 178478839HCID 178478839, compound

Product 1

HCID 69903148HCID 69903148, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Analogously to Example 2, 0.3 g of Raney nickel is added to a mixture of 1.0 g (2.13 mmol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(2-naphthyl)-imidazole dihydrochloride in 120 ml of methanol/water (1:1), and hydrogenation is carried out at room temperature and under normal pressure until the absorption of hydrogen has ceased. The reaction mixture is then filtered, the filtrate is acidified to pH 3 with 3N methanolic hydrochloric acid, and concentration is carried out by evaporation in vacuo. Recrystallization of the residue from ethanol with the addition of a small amount of methanol yields the title compound, m.p. >280° C., 1H-NMR (DMSO/D2O): δ=8.31 (d, 1H); 8.18 (s, 1H); 8.05 (s, 1H); 7.92-8.03 (m, 3H); 7.79-7.86 (m, 2H); 7.52-7.69 (m, 3H); 3.35 (s, 4H).

Workup

  1. customis carried out at room temperature and under normal pressure until the absorption of hydrogen
  2. filtrationThe reaction mixture is then filtered
  3. concentrationthe filtrate is acidified to pH 3 with 3N methanolic hydrochloric acid, and concentration
  4. customis carried out by evaporation in vacuo
  5. customRecrystallization of the residue from ethanol
  6. additionwith the addition of a small amount of methanol

Sources & evidence

ORD record
ord-21f2f7e3bc6941088e33c613e419cbac
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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