1-(4-Fluorophenyl)piperazine → 4-{-Ethyl-7-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-1H-imidazo[4,5-c]pyridin-2-yl)furazan-3-ylamine

HRID 1394203Notes

Reaction equation

HRID 1394203 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:24][CH3:25])[C:9]3[C:14]([CH2:15][NH:16]C4CCNCC4)=[CH:13][N:12]=[CH:11][C:10]=3[N:23]=2)=[N:4][O:5][N:6]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37]N[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH2:24]([N:8]1[C:9]2[C:14]([CH2:15][N:16]3[CH2:35][CH2:34][N:33]([C:30]4[CH:29]=[CH:28][C:27]([F:26])=[CH:32][CH:31]=4)[CH2:38][CH2:37]3)=[CH:13][N:12]=[CH:11][C:10]=2[N:23]=[C:7]1[C:3]1[C:2]([NH2:1])=[N:6][O:5][N:4]=1)[CH3:25]

Participants

6

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 11393719SB-747651A

Product 1

HCID 596818234-{-Ethyl-7-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-1H-imidazo[4,5-c]pyridin-2-yl)furazan-3-ylamine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 191 Step 1 (0.10 g, 0.38 mmole) in 1,2-dichloroethane (5 ml) was treated with 1-(4-fluorophenyl)piperazine (0.10 g, 0.58 mmole) and stirred at ambient temperature for 15 minutes. Sodium triacetoxyborohydride (0.16 g, 0.76 mmole) was added and the reaction mixture stirred at ambient temperature for 18 hours. The mixture was diluted with dichloromethane, washed (×2) with saturated sodium hydrogen carbonate solution followed by saturated brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford the title compound; MS (ES+) m/e 357 [M+H]+. The following examples were prepared from the product of Example 191 Step 1 using the method described in Example 200.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 18 hours
  2. washwashed (×2) with saturated sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-661d35329b5f41e787b86d893f324ecf
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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