Tetrahydrofuran → 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

HRID 2192962ノート

反応式

HRID 2192962 の反応式
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12](Cl)[N:11]=[CH:10][CH:9]=3.C1C[O:29]CC1>Cl.CCOC(C)=O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([NH:15][C@@H:16]([C:20]([F:23])([F:22])[F:21])[CH:17]([CH3:19])[CH3:18])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:29])[C:13]=3[C:4]=2[CH:3]=1

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 593755309-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine

生成物 1

HCID 249053779-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

9-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine (1.0 g, 2.31 mmol) in 6 N HCl (4 mL) and THF (4 mL) was heated to 90° C. for 2 hr. The reaction was cooled and diluted with EtOAc and quenched with sat. NaHCO3. The mixture was extracted and the organic layers were separated, dried with MgSO4, filtered, and concentrated to give the crude product. Column chromatography on silica gel 100% Hex. to 100% EtOAc afforded 9-bromo-6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 10.1 (d, 1H), 8.31 (d, 1H), 7.75 (d, 1H), 7.40 (d, 1H), 6.65, (d, 1H), 5.46 (m, 1H), 2.35 (m, 1H), 1.12 (d, 3H), 1.06 (d, 3H). LRMS (ESI) calc'd for (C17H16BrF3N3O) [M+H]+, 414.0; found 414.0.

後処理

  1. temperatureThe reaction was cooled
  2. customquenched with sat. NaHCO3
  3. extractionThe mixture was extracted
  4. customthe organic layers were separated
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product

出典と根拠

ORDレコード
ord-efe21f3b208d4767a03cff0712b273f6
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

読み込み中…