Ammonia → HCID 22393781, compound

HRID 1071652Notes

Reaction equation

HRID 1071652 reaction equation
[C:1]([C:3]([C:27]1[CH:31]=[C:30](Br)[S:29][C:28]=1[Br:33])([CH:24]([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:9][CH2:8]1)#[N:2].[CH3:34][N:35](C)C=O.O.N>[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)C>[C:1]([C:3]([C:27]1[CH:31]=[C:30]([C:34]#[N:35])[S:29][C:28]=1[Br:33])([CH:24]([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:11][CH2:12]1)#[N:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 962Water2×HCID 6228DimethylformamideHCID 22393623HCID 22393623, compound

Product 1

HCID 22393781HCID 22393781, compoundYield 6.7%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

In a nitrogen atmosphere, 1-(4-cyano-5-methyl-4-[(2,5-dibromo)-3-thienyl]hexyl)-4-[2-(3-cyanophenoxy) ethyl] piperazine (145 mg) was dissolved in a mixed solvent of dimethylformamide (10 mL)/water (0.1 mL) of zinc cyanide (57.3 mg) and 1,1′-bis(diphenylphosphino)ferrocene (13.5 mg). Palladium-dibenzylidene acetone complex (8.9 mg) was added thereto, the atmosphere of the mixture was replaced 3 times with nitrogen, and then the solution was stirred at 120° C. for 4 hours. Water, diethyl ether and an aqueous ammonia were added thereto, to separate the organic layer. The resulting organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. After filtering off the drying agent, the filtrate was evaporated, and the residue was purified by LC-MS (ODS column; acetonitrile/water system), to give the title compound as a yellow oil (8 mg, 6.7%).

Workup

  1. additionPalladium-dibenzylidene acetone complex (8.9 mg) was added
  2. customto separate the organic layer
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the drying agent
  6. customthe filtrate was evaporated
  7. customthe residue was purified by LC-MS (ODS column; acetonitrile/water system)

Sources & evidence

ORD record
ord-e9c3135a0ea5408c82445d023d9453bd
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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