Acefylline → HCID 45254481, 화합물

HRID 1924361

반응식

HRID 1924361 반응식
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]([OH:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=1>CN(C=O)C.CS(C)=O>[CH3:2][N:1]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([NH:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]([OH:52])([CH3:50])[CH3:51])=[CH:47][CH:48]=3)=[O:17])[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4]

참가 물질

5

반응물 3

HCID 69550AcefyllineHCID 95432612-(4-Aminophenyl)propan-2-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 45254481HCID 45254481, 화합물

시약·촉매·용매 1

HCID 3013483N,N-dimethylformamide; methylsulfinylmethane용매

실험 절차

To a 0° C. solution of acid 101 (0.32 g, 1.34 mmol) in DMF/DMSO (1:1, 20 mL) was added HATU (0.0.76 g, 2.01 mmol). The reaction was then stirred an additional 15 min at room temperature. The solution was cooled to 0° C. and amine 135 (0.30 g, 2.01 mmol) was added. The reaction was then stirred at rt overnight. The DMF was concentrated in vacuo and water was added to the reaction. The aqueous layer was extracted with EtOAc The ethyl acetate layer was then washed again with water and the organic layer was concentrated in vacuo. The product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH to yield 402 as a pure light brown semi solid (0.086 g, 17.5%). MS (APCI): m/z 372.2 [M−H]+ Anal. Calcd. For C18H21N5O4.0.35 EtOAc: C, 57.93; H, 5.96; N, 17.41. Found C, 58.36; H, 6.14; N, 16.96.

후처리

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe reaction was then stirred at rt overnight
  3. concentrationThe DMF was concentrated in vacuo and water
  4. additionwas added to the reaction
  5. extractionThe aqueous layer was extracted with EtOAc The ethyl acetate layer
  6. washwas then washed again with water
  7. concentrationthe organic layer was concentrated in vacuo
  8. customThe product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes and EtOAc/MeOH

출처 및 근거

ORD 기록
ord-4a87810f3cad42199263f2c353b9faf7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178542B2

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