Diisopropylethylamine → 1-[4-(4-Fluoro-2-trifluoromethyl-benzoyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy]-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029182ノート

反応式

HRID 1029182 の反応式
[O:1]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16](=[O:22])[NH:17]4)[CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[C:30]([C:37]([F:40])([F:39])[F:38])[CH:29]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[F:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:4]2[C:5]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:21]=[CH:20][N:19]=[C:18]5[C:13]=4[C:14]4[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=4[C:16](=[O:22])[NH:17]5)=[CH:7][C:6]=3[O:1][CH2:2][CH2:3]2)=[O:33])=[C:30]([C:37]([F:38])([F:39])[F:40])[CH:29]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

生成物 1

HCID 581683171-[4-(4-Fluoro-2-trifluoromethyl-benzoyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy]-5H-benzo[c][1,8]naphthyridin-6-one収率 37.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Compound 218 (50 mg, 0.14 mmol), 4-fluoro-2-trifluoromethyl-benzoyl chloride (49 mg, 0.22 mmol), and DIEA (0.07 mL, 0.43 mmol) were dissolved in dioxane (2 mL) and stirred for 1 h at room temperature. The reaction was quenched with H2O, diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 100% EtOAc in hexanes to provide 219 (28 mg, 36% yield) as a tan solid. LC-MS (M+H=536, obsd.=536).

後処理

  1. customThe reaction was quenched with H2O
  2. additiondiluted with EtOAc
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with EtOAc
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified via Biotage
  7. washeluting with a gradient of 0 to 100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-311809829cac4e0fbf0367e19400e909
出典データセット
uspto-grants-2014_05
特許番号
US08735584B2

反応ノート

読み込み中…