Triethylamine → 2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide

HRID 1616123노트

반응식

HRID 1616123 반응식
[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([C:13]([OH:15])=O)=[CH:7][CH:8]=2)[NH:3]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.[O:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]1[O:44][NH2:45]>O.CN(C=O)C>[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([C:13]([NH:45][O:44][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][O:38]3)=[O:15])=[CH:7][CH:8]=2)[NH:3]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 196042892,4-Dihydroxyquinazoline-7-carboxylic acid

생성물 1

HCID 866642012,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid (0.15 g, 0.73 mmol), DMF (2.80 mL), triethylamine (0.30 mL, 2.2 mmol) and fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (0.25 g, 0.95 mmol) was stirred for 15 min and O-(tetrahydropyran-2-yl)hydroxylamine (0.10 g, 0.87 mmol) was added. The reaction mixture was stirred at rt for 1 d. Water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford 2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide (0.15 g, 68%). LC-MS: (FA) ES+ 306.

후처리

  1. stirringThe reaction mixture was stirred at rt for 1 d
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-69ef4a07c99641daae4a46b6e765bad0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765773B2

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