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 1862453노트

반응식

HRID 1862453 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-634d9e0187a54eb6a51afa4df6965e22
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06538004B2

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