HCID 22136482, compound → HCID 10205666, compound

HRID 1827268Notes

Reaction equation

HRID 1827268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)([C:20]4[N:24]([CH3:25])[C:23](SC)=[N:22][N:21]=4)[NH2:19])[CH:16]=3)[N:11]=[C:10]([CH3:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1>[Ni].CC(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:28]4[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=4)([C:20]4[N:24]([CH3:25])[CH:23]=[N:22][N:21]=4)[NH2:19])[CH:16]=3)[N:11]=[C:10]([CH3:35])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22136482HCID 22136482, compound

Product 1

HCID 10205666HCID 10205666, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 180AcetoneSolvent

Procedure

Raney Nickel was added at room temperature to a mixture of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-methyl-α-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]-6-quinolinemethanamine (0.0012 mol), obtained in Example B16, in 2-propanone (40 ml) under N2 flow. The mixture was stirred at room temperature for 3 hours, filtered over celite, rinsed with DCM and the solvent was evaporated till dryness. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried. The residue (0.31 g, 52%) was purified twice by column chromatography over kromasil (eluent: CH3OH/H2O 80/20 then CH3CN/H2O 35/65; 10 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.13 g (22%) of 4-(3-chlorophenyl)-α-(4-chlorophenyl)-2-methyl-α-(4-methyl-4H-1,2,4-triazol-3-yl)-6-quinolinemethanamine, MS (ESI) m/z: 474 476 478.

Workup

  1. filtrationfiltered over celite
  2. washrinsed with DCM
  3. customthe solvent was evaporated till dryness
  4. customThe residue was crystallized from diethyl ether
  5. filtrationThe precipitate was filtered off
  6. customdried
  7. customThe residue (0.31 g, 52%) was purified twice by column chromatography over kromasil (eluent
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bcff3765c00e4469b0a4e213dc07bcbc
Source dataset
uspto-grants-2006_05
Patent number
US07053105B2

Reaction notes

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