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 1837105ノート

反応式

HRID 1837105 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fdea4cca02a445eab620436430a3a202
出典データセット
uspto-grants-2004_08
特許番号
US06780872B2

反応ノート

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