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

HRID 1623841
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HRID 1623841 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 30720221(2R,6S)-1,2,6-TrimethylpiperazineHCID 369825032-(benzyloxy)-5-bromo-N-(pyridin-3-yl)benzamide

생성물 1

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

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-a472b823caff4ec7983ea2a51e9c080b
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778939B2

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