Dimethylformamide → HCID 59253657, compound

HRID 1258144Notes

Reaction equation

HRID 1258144 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][N:23](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]=[N:17][C:18]([C:22]#[N:23])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 28530649HCID 28530649, compound

Product 1

HCID 59253657HCID 59253657, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
160 °C

Procedure

A mixture of (1-benzyl-piperidin-4-yl)-(6-chloro-pyridazin-3-yl)-amine (D1) (3 g, 9.9 mmol), zinc cyanide (2.09 g, 17.8 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.74 g, 2.3 mmol) in N,N-dimethylformamide (30 ml) was heated at 160° C. for 30 min., under microwave irradiation (Milestone MW-oven). The solvent was then evaporated in vacuo and an aqueous solution of potassium carbonate (10%) and ethyl acetate were added. The organic phase was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica gel; 0 to 1.5% ammonia in methanol (7M)/dichloromethane) and then by HPLC to yield D2 (1.06 g, 36%) as a solid. C17H19N5 requires 293. Found 294 (MH+).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionan aqueous solution of potassium carbonate (10%) and ethyl acetate were added
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by column chromatography (silica gel; 0 to 1.5% ammonia in methanol (7M)/dichloromethane)

Sources & evidence

ORD record
ord-a62e9f4807404cc9965a05a29574c2e4
Source dataset
uspto-grants-2013_06
Patent number
US08466153B2

Reaction notes

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