2H-pyran-3,5(4H,6H)-dione → 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

HRID 1837105노트

반응식

HRID 1837105 반응식
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[C:18]([F:21])([F:20])[F:19].[O:22]1[CH2:27][C:26](=O)[CH2:25][C:24](=[O:29])[CH2:23]1>C(O)C>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:25]3[C:24](=[O:29])[CH2:23][O:22][CH2:27][C:26]=3[NH:1][C:2]3[N:3]([CH3:8])[O:4][C:5](=[O:7])[C:6]2=3)=[CH:12][C:11]=1[C:18]([F:21])([F:20])[F:19]

참가 물질

5

반응물 3

HCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

생성물 1

HCID 101568394-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The product from Example 45A (0.11 g, 1 mmol), 4-fluoro-3-trifluromethylbenzaldehyde and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) were heated in 2 mL of ethanol for 2 days. The reaction mixture was evaporated under reduced pressure and the remaining residue was triturated with methylene chloride. The resulting precipitate was filtered to provide the title compound as the filter cake. 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 4.07 (s, 2H), 4.58 (q, 2H), 4.87 (s, 1H), 7.42 (t, 1H), 7.59 (m, 2H), 10.8 (s, 1H); MS (ESI) m/z 383 (M−H)−; Anal. Calcd for C16H12N2F4O4: C, 51.61; H, 3.22; N, 7.52. Found: C, 51.09; H, 3.11; N, 6.98.

후처리

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe remaining residue was triturated with methylene chloride
  3. filtrationThe resulting precipitate was filtered

출처 및 근거

ORD 기록
ord-fdea4cca02a445eab620436430a3a202
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780872B2

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