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Pyridine → N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

HRID 1799460
ノート
印刷プレビュー

反応式

HRID 1799460 の反応式
[Br:1][C:2]1[C:3](=[O:21])[N:4]([CH2:9][C:10]2[CH:20]=[CH:19][C:13]3[O:14][C:15]([F:18])([F:17])[O:16][C:12]=3[CH:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.[C:22]([NH:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:24])[CH3:23].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C=O)C>[Br:1][C:2]1[C:3](=[O:21])[N:4]([CH2:9][C:10]2[CH:20]=[CH:19][C:13]3[O:14][C:15]([F:17])([F:18])[O:16][C:12]=3[CH:11]=2)[C:5](=[O:8])[N:6]([C:30]2[CH:31]=[C:26]([NH:25][C:22](=[O:24])[CH3:23])[CH:27]=[CH:28][CH:29]=2)[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049PyridineHCID 157274(3-Acetamidophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 686982866-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-1,2,4-triazine-3,5(2H,4H)-dione

生成物 1

HCID 68701252N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide収率 61%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

According to Scheme 2 Step 3: A mixture of 6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-1,2,4-triazine-3,5(2H,4H)-dione (300 mg, 0.83 mmol), DMF (5 mL), 3-acetamidophenylboronic acid (222 mg, 1.24 mmol), copper acetate (150 mg, 0.83 mmol) and pyridine (135 μl, 1.66 mmol) was stirred at 65° C. for 15 hours under room atmosphere. A saturated solution of NaHCO3 (200 mL) was added and the aqueous layer was extracted thrice with 200 mL of DCM. The organic layers were combined to be dried over MgSO4, filtered and concentrated under reduced pressure to afford a brown solid. The crude solid was purified by flash chromatography with silica gel (AIT Flashmart 25 g prepacked column C18) using water/acetonitrile 6/4 as eluant to afford N-(3-(6-bromo-4-((2,2-difluorobenzo[d][1,3]dioxol-5-yl)methyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (250 mg, 61%) as a white solid.

後処理

  1. extractionthe aqueous layer was extracted thrice with 200 mL of DCM
  2. dry with materialto be dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford a brown solid
  6. customThe crude solid was purified by flash chromatography with silica gel (AIT Flashmart 25 g prepacked column C18)

出典と根拠

ORDレコード
ord-ca40bff29aa0435083f97ceaa7a9710c
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08344138B2

反応ノート

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