Triethylamine → 2-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide

HRID 2092070ノート

反応式

HRID 2092070 の反応式
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([OH:13])=O)[C:6](=[O:9])[C:7]=1[Br:8].C(Cl)(=O)C(Cl)=O.[N:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1.C(N(CC)CC)C>O1CCCC1.CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][C:11]([NH:27][CH2:26][C:23]2[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=2)=[O:13])[C:6](=[O:9])[C:7]=1[Br:8]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 773174-PyridinemethanamineHCID 595741422-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)acetic acid

生成物 1

HCID 595743872-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)-N-(pyridin-4-ylmethyl)acetamide収率 33%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-(4,5-Dibromo-6-oxopyridazin-1(6H)-yl)acetic acid (1.48 g, 4.38 mmol) in tetrahydrofuran (30 mL) was mixed with N,N-dimethylformamide (1 drop) and oxalyl chloride (570 μL, 6.53 mmol) at room temperature and stirred at room temperature for 30 minutes. The solvent was removed by distillation, and the residue was dissolved in tetrahydrofuran (10 mL) and added dropwise to 4-picolylamine (538 μL, 5.22 mmol) and triethylamine (1.22 mL, 8.70 mmol) in tetrahydrofuran (20 mL) and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was mixed with water and extracted with chloroform three times, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting solid was washed with 2-propanol-hexane to give the desired product (572 mg, 33% yield).

後処理

  1. customThe solvent was removed by distillation
  2. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  3. stirringstirred at room temperature for 30 minutes
  4. customAfter completion of the reaction
  5. extractionextracted with chloroform three times
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. washThe resulting solid was washed with 2-propanol-hexane

出典と根拠

ORDレコード
ord-d7528680d4874bf5ab02e9b23cf7c1d0
出典データセット
uspto-grants-2013_05
特許番号
US08440666B2

反応ノート

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