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Cesium carbonate → 6-(3-chloro-4-fluorobenzyl)4-[(3-chloro-4-fluorobenzyl)oxy]-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

HRID 1817323
ノート
印刷プレビュー

反応式

HRID 1817323 の反応式
[OH:1][C:2]1[C:3](=[O:19])[N:4]([CH3:18])[C:5]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[C:6]2[C:11]=1[C:10](=O)[NH:9][CH2:8][CH2:7]2.[C:20]([O-:23])([O-])=O.[Cs+].[Cs+].[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:30]Br.[H-].[Na+]>CN(C=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:10][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([O:1][CH2:30][C:29]3[CH:32]=[CH:33][C:34]([F:35])=[C:27]([Cl:26])[CH:28]=3)[C:3](=[O:19])[N:4]([CH3:18])[C:5]=2[C:13]([N:15]([CH3:16])[CH3:17])=[O:14])[C:20]1=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 27575424-(Bromomethyl)-2-chloro-1-fluorobenzeneHCID 690584564-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

生成物 1

HCID 690581956-(3-chloro-4-fluorobenzyl)4-[(3-chloro-4-fluorobenzyl)oxy]-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

A solution of 4-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.018 g, 0.068 mmol) in DMF (2 mL) was treated with Cs2CO3 (0.066 g, 0.2 mmol) and 3-chloro-4-fluoro benzyl bromide (0.045 g, 0.2 mmol) and heated to 40° C. The reaction mixture was then cooled to 0 degrees C., a suspension of NaH (95% dispersion in oil, 0.2 mmol) was added and the reaction was warmed to room temperature. After 1 hr the reaction was partitioned between ice water and EtOAc, the organic layer was dried with brine and Na2SO4, filtered and evaporated to give 6-(3-chloro-4-fluorobenzyl)4-[(3-chloro-4-fluorobenzyl)oxy]-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (ES MS M+1=549.9). This material was then dissolved in CH2Cl2 (3 mL) and treated with 4 drops of a 30% by weight solution of HBr in propionic acid at room temperature. After 20 minutes the solution was concentrated and purified by reverse phase chromatography to give the product.

後処理

  1. temperatureThe reaction mixture was then cooled to 0 degrees C
  2. additionwas added
  3. temperaturethe reaction was warmed to room temperature
  4. customAfter 1 hr the reaction was partitioned between ice water and EtOAc
  5. dry with materialthe organic layer was dried with brine and Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-a5bb6bcf145b42ff92478210191a9974
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07598264B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート