Dimethylformamide → N-(2-fluorophenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamide

HRID 1924355

반응식

HRID 1924355 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=N[C:28]2[CH:29]=[CH:30][CH:31]=N[C:27]1=2)=[N+](C)C)C.[F:35][P-](F)(F)(F)(F)F.CCO[C:45]([CH3:47])=O.C[N:49]([CH:51]=O)C>>[F:35][C:45]1[CH:47]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:27][CH2:51][NH:49][C:15](=[O:17])[CH2:14][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 69550AcefyllineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 28010248N-(2-fluorophenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamide수율 31%

실험 절차

Compound 101 (600 mg, 2.5 mmol) was mixed with HATU (1.14 g, 3.0 mmol) in 20 mL of DMF under N2 and stirred at room temperature for 20 min. Compound 117 (0.33 mL, 2.5 mmol) was added. The resulting mixture was stirred overnight. EtOAc (100 mL) was added and the resulting solution was washed with water (3×80 mL) and brine (80 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes. The purified product was triturated with ether (30 mL) and filtered to yield 404 as a white solid (281 mg, 31%). MS (APCI): m/z 360 [M+H]+. Anal. Calcd for C17H18FN5O3.0.3H2O: C, 55.98; H, 5.14; N, 19.20. Found: C, 55.87; H, 5.07; N, 19.13.

후처리

  1. stirringThe resulting mixture was stirred overnight
  2. washthe resulting solution was washed with water (3×80 mL) and brine (80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes
  7. customThe purified product was triturated with ether (30 mL)
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-911620a3621c4110b8084bd78112f613
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178542B2

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