Cesium carbonate → 3-(5-(4-Cyclobutyl-1,4-diazepane-1-carbonyl)pyridin-2-yloxy)benzonitrile

HRID 404548ノート

反応式

HRID 404548 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:27]([C:29]1[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=1)#[N:28].[OH-].[Na+]>CC(N(C)C)=O.CC(OC)(C)C>[CH:17]1([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:35][C:31]4[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=4)[C:27]#[N:28])=[N:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)[CH2:20][CH2:19][CH2:18]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 133943-CyanophenolHCID 14798Sodium HydroxideHCID 58076653(6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

生成物 1

HCID 236243123-(5-(4-Cyclobutyl-1,4-diazepane-1-carbonyl)pyridin-2-yloxy)benzonitrile

試薬・触媒・溶媒 2

HCID 15413tert-Butyl methyl ether溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
125 °C

実験手順

To a solution of (6-chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone (101.0 g, 343.8 mmol) in dimethylacetamide (1.1 L) was added Cs2CO3 (224 g, 687.6 mmol) and m-cyanophenol (81.9 g, 687.6 mmol). The resulting mixture was warmed to 125° C. and stirred for 20 h. After cooling to room temperature, the resulting mixture was filtered and acetic acid (1.5 L) was added to the filtrate. The resulting mixture was concentrated under reduced pressure to yield a brown residue which was taken up into MTBE (1.5 L) and 1N NaOH(aq) (1.5 L). The resulting layers were thoroughly mixed and then separated. The organic extract was dried over magnesium sulfate, filtered, and concentrated to yield the title compound as a brown oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting mixture was filtered
  3. additionacetic acid (1.5 L) was added to the filtrate
  4. concentrationThe resulting mixture was concentrated under reduced pressure
  5. customto yield a brown residue which
  6. additionThe resulting layers were thoroughly mixed
  7. customseparated
  8. extractionThe organic extract
  9. dry with materialwas dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-80205d6f699f418e953a6e26290db706
出典データセット
uspto-grants-2014_06
特許番号
US08748596B2

反応ノート

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