Potassium Carbonate → Ethyl 6-bromo-1-(1-methylazetidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

HRID 1047174ノート

反応式

HRID 1047174 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:17](F)=[CH:18][N:19]=1)[C:5]([C:7](=[CH:13][N:14]([CH3:16])C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].Cl.[CH3:22][N:23]1[CH2:26]C(N)[CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][N:19]=1)[N:14]([CH:16]1[CH2:24][N:23]([CH3:26])[CH2:22]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 670505831-Methylazetidin-3-amine xhydrochlorideHCID 86665047Ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate2 回

生成物 1

HCID 86665054Ethyl 6-bromo-1-(1-methylazetidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate収率 163.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 66, 0.690 g, 2 mmol, 1 equiv.) in THF (7 mL) was added 1-methylazetidin-3-amine HCl (245 mg, 2 mmol, 1 equiv.) and potassium carbonate (276 mg, 2 mmol, 1 equiv.). This reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure and re-suspended in DMF (7 mL). Potassium carbonate (553 mg, 4 mmol, 2 equiv.) was added, and the reaction mixture was stirred at 70° C. for 3 h. The reaction mixture was cooled to room temperature and quenched with water. 1 N HCl was added until pH 4-5 was reached. The precipitate was washed with water and hexanes and dried to provide ethyl 6-bromo-1-(1-methylazetidin-3-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate (1.2 g, ≧99%). Calcd for C15H16BrN3O3 [M+H]+: 367.91.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe reaction mixture was stirred at 70° C. for 3 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with water
  5. addition1 N HCl was added until pH 4-5
  6. washThe precipitate was washed with water and hexanes
  7. customdried

出典と根拠

ORDレコード
ord-77e0c54e6aeb4b21ab23b83f019c250c
出典データセット
uspto-grants-2013_10
特許番号
US08569484B2

反応ノート

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