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Dimethylformamide → 3-[5-Fluoro-3-(tetrahydro-pyran-4-YL)-pyridin-2-yloxy]-cyclobutanecarboxylic acid methoxy-methyl-amide

HRID 1846789
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HRID 1846789 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]([O:8][CH:9]2[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10]2)=[N:6][CH:7]=1.CN([CH:25]=[O:26])C.[CH2:27]([N:29](CC)CC)C>O.CCOC(C)=O>[CH3:25][O:26][N:29]([CH3:27])[C:13]([CH:11]1[CH2:10][CH:9]([O:8][C:5]2[C:4]([CH:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)=[CH:3][C:2]([F:1])=[CH:7][N:6]=2)[CH2:12]1)=[O:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 585486643-[5-Fluoro-3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclobutanecarboxylic acid

생성물 1

HCID 585485673-[5-Fluoro-3-(tetrahydro-pyran-4-YL)-pyridin-2-yloxy]-cyclobutanecarboxylic acid methoxy-methyl-amide

시약·촉매·용매 2

HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of 3-[5-fluoro-3-(tetrahydro-pyran-4-yl)-pyridin-2-yloxy]-cyclobutanecarboxylic acid (1.5 g, 4.68 mmol) was added DMF (20 mL), triethylamine (1 mL, 7.02 mmol), and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (2.24 g, 5.90 mmol). The reaction mixture was stirred at RT for 1d. Then it was diluted with water and EtOAc. The organic layer was separated and the aqueous phase was extracted with EtOAc (2×10 mL). All the organic layers were combined and washed with brine (1×10 mL), dried over MgSO4, filtered, and concentrated to get a crude, which was purified by flash column chromatography on silica gel (30% to 70% EtOAc in hexanes) to give the product (2.2 g) as yellow oil.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×10 mL)
  3. washwashed with brine (1×10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto get a crude, which
  8. customwas purified by flash column chromatography on silica gel (30% to 70% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-142f47cf0368442e91b6656311468350
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952037B2

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