HCID 21082055, compound → HCID 21082077, compound

HRID 347017Notes

Reaction equation

HRID 347017 reaction equation
[NH2:1][C:2]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH3:27])[C:22](=[O:28])[CH:21]=[C:20]2[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)([C:11]1[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=1)[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1>[Ni].CO.N>[NH2:1][C:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH2:8])=[CH:9][CH:10]=1)([C:11]1[N:15]([CH3:16])[CH:14]=[N:13][CH:12]=1)[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH3:27])[C:22](=[O:28])[CH:21]=[C:20]2[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1

Participants

4

Reactant 1

HCID 21082055HCID 21082055, compound

Product 1

HCID 21082077HCID 21082077, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

Raney nickel (0.55 g) was added to a mixture of 4-[amino[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl](1-methyl-1H-imidazol-5-yl)methyl]-benzonitrile, (0.0011 mol) in CH3OH/NH3 7N (12 ml) under N2 flow. The mixture was hydrogenated overnight under a 5 bar pressure, then filtered over celite. The filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/0.5; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.36 g (65%)g of 6-[amino[4-(aminomethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone, mp. 150° C.

Workup

  1. filtrationfiltered over celite
  2. customThe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 92/8/0.5; 15–40 μm)
  4. customThe pure fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-46f73903300f47aabd21df76907bea07
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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