Dimethylacetamide → HCID 86708519、化合物

HRID 1430805ノート

反応式

HRID 1430805 の反応式
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

参加物

6

反応物 2

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

生成物 1

HCID 86708519HCID 86708519、化合物

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 178418851HCID 178418851、化合物触媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4fc8679ddeb94dee8498ca304ea696cc
出典データセット
uspto-grants-2015_01
特許番号
US08940736B2

反応ノート

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