Dimethylacetamide → HCID 86708519, compound

HRID 921636Notes

Reaction equation

HRID 921636 reaction equation
Br[C:2]1[N:10]2[C:5]([C:6]([N:15]([CH:25]3[CH2:27][CH2:26]3)[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:9]2)=[N:4][CH:3]=1.C[C:29]([N:31](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:25]1([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:6]2[C:5]3=[N:4][CH:3]=[C:2]([C:29]#[N:31])[N:10]3[N:9]=[C:8]([S:11]([CH3:14])(=[O:13])=[O:12])[N:7]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 899201847-bromo-N-cyclopropyl-N-(4-methoxybenzyl)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 86708519HCID 86708519, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418851HCID 178418851, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

In a round-bottom flask, a mixture of 7-bromo-N-cyclopropyl-N-(4-methoxybenzyl)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazin-4-amine (0.115 g, 0.254 mmol), zinc cyanide (0.021 g, 0.178 mmol), and zinc powder (4.99 mg, 0.076 mmol) in DMA (30 mL) was degassed by evacuating with vacuum and back filling with nitrogen. The mixture was treated with bis(tri-t-butylphosphine)palladium (0) (0.026 g, 0.051 mmol), degassed again as described above, and the reaction was heated at 100° C. for 4 hours. The reaction mixture was filtered and the filtrate diluted with ethyl acetate, washed with water, brine, dried with sodium sulfate and concentrated in vacuo. The crude product mixture was purified via ISCO (0-15% of methanol/dichloromethane in 20 minutes, 40 g silica column) to give the pure product 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (75 mg).

Workup

  1. customwas degassed
  2. customby evacuating with vacuum
  3. customdegassed again
  4. filtrationThe reaction mixture was filtered
  5. additionthe filtrate diluted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product mixture was purified via ISCO (0-15% of methanol/dichloromethane in 20 minutes, 40 g silica column)

Sources & evidence

ORD record
ord-97baf8d9155c4d2e84e8ca8f01839756
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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