HCID 178478843, compound → HCID 69903241, compound

HRID 357606Notes

Reaction equation

HRID 357606 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]([F:28])=[CH:24][CH:23]=2)[N:19]=[C:18]1[NH2:29])=[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:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[N:19]=[C:18]1[NH2:29])(=[NH:4])[NH2:6]

Participants

4

Reactant 1

HCID 178478843HCID 178478843, compound

Product 1

HCID 69903241HCID 69903241, compound

Reagents, catalysts & solvents 2

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

Procedure

Analogously to Example 2, 0.25 g of Raney nickel is added to a solution of 1.0 g (2.105 mmol) of 1-[4-(N-hydroxyamidino)-2,3-dihydro-1H-inden-1-ylideneamino]-2-amino-4-(4-fluorophenyl)-imidazole dihydrochloride in 70 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. The crystalline residue is recrystallized from methanol/diethyl ether, yielding the title compound with a water content of 4.88%, m.p. 245°-250° C. (decomp.), 1H-NMR (D2O): δ=8.09 (d, 1H); 7.81 (d, 1H); 7.44-7.61 (m, 3H); 7.42 (s, 1H); 7.03-7.15 (m, 2H); 3.27-3.33 (m, 2H); 3.11-3.17 (m, 2H).

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. customThe crystalline residue is recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-7dd0de3480264642ae513421925f287f
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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