1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxyphenyl)-imidazole dihydrochloride → 1-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxvphenyl)-imidazole dihydrochloride

HRID 357592Notes

Reaction equation

HRID 357592 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:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:30])=[NH:6]>[Ni].CO>[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:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[N:19]=[C:18]1[NH2:30])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 1784887961-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxyphenyl)-imidazole dihydrochloride

Product 1

HCID 699043811-[4-(Amidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxvphenyl)-imidazole dihydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Analogously to Example 2, approximately 2 g of Raney nickel are added to a solution of 5.8 g (0.00129 mol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-methoxyphenyl)-imidazole dihydrochloride in 600 ml of methanol, 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 and the filtrate is concentrated. The product that has crystallised out is filtered off with suction and recrystallized from methanol, yielding the title compound in the form of the monohydrate, m.p. >220° C., 1H-NMR (DMSO): δ=9.56 (d, 4H); 8.33 (d, 1H); 7.99 (s, 1H); 7.94 (s, 2H); 7.75-7.84 (m, 3H); 7.64 (t, 1H); 7.04 (d, 2H); 3.80 (s, 3H), 3.40 (m, 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 concentrated
  4. customThe product that has crystallised out
  5. filtrationis filtered off with suction
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-c23f041aa4ca4f4daeed647d7eb75156
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

Loading…