Dimethylacetamide → HCID 86708519, 화합물

HRID 921636노트

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HRID 921636 반응식
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

참가 물질

6

반응물 2

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

생성물 1

HCID 86708519HCID 86708519, 화합물

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 178418851HCID 178418851, 화합물촉매

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-97baf8d9155c4d2e84e8ca8f01839756
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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