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Cesium carbonate → 2-[(Phenylmethyl)oxy]-N-3-pyridinyl-5-[(3R,5S)-3,4,5-trimethyl-1-piperazinyl]benzamide

HRID 1623841
ノート
印刷プレビュー

反応式

HRID 1623841 の反応式
[CH3:1][N:2]1[C@@H:7]([CH3:8])[CH2:6][NH:5][CH2:4][C@H:3]1[CH3:9].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:63]1[CH:64]=[CH:65][C:66]([O:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)=[C:67]([CH:77]=1)[C:68]([NH:70][C:71]1[CH:72]=[N:73][CH:74]=[CH:75][CH:76]=1)=[O:69]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:80]1([CH2:79][O:78][C:66]2[CH:65]=[CH:64][C:63]([N:5]3[CH2:6][C@H:7]([CH3:8])[N:2]([CH3:1])[C@H:3]([CH3:9])[CH2:4]3)=[CH:77][C:67]=2[C:68]([NH:70][C:71]2[CH:72]=[N:73][CH:74]=[CH:75][CH:76]=2)=[O:69])[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=1
参加物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 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 30720221(2R,6S)-1,2,6-TrimethylpiperazineHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

生成物 1

HCID 699370442-[(Phenylmethyl)oxy]-N-3-pyridinyl-5-[(3R,5S)-3,4,5-trimethyl-1-piperazinyl]benzamide

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒

実験手順

(2R,6S)-1,2,6-Trimethylpiperazine (105 mg, 0.52 mmol), cesium carbonate (680 mg, 2.09 mmol), BINAP (2.44 mg, 3.91 μmol) and Pd2(dba)3 (1.20 mg, 1.30 μmol) were added to 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 200 mg, 0.52 mmol) in anhydrous toluene (5 ml), and the mixture was heated to reflux overnight. The reaction mixture was evaporated under reduced pressure. Water (50 ml) was added to the residue and the mixture was extracted with ethyl acetate (3×50 ml). The organics were combined and evaporated, and the residue purified by MDAP twice to yield the title compound. 180 mg.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additionWater (50 ml) was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  6. customevaporated
  7. customthe residue purified by MDAP twice

出典と根拠

ORDレコード
ord-a472b823caff4ec7983ea2a51e9c080b
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778939B2

反応ノート

読み込み中…

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