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Sodium hydride → 2-anilino-7-[2-(2-oxo-1-pyrrolidinyl)ethoxy]-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one

HRID 1063549
ノート
印刷プレビュー

反応式

HRID 1063549 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].[NH:12]([C:19]1[N:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:21]2[C:26]([C:27](=[O:29])[CH:28]=1)=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=[C:23](Cl)[N:22]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[NH:12]([C:19]1[N:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:21]2[C:26]([C:27](=[O:29])[CH:28]=1)=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=[C:23]([O:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[N:22]=2)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
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

5

反応物 3

HCID 24758Sodium hydrideHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 219481692-anilino-7-chloro-1-phenyl-5-trifluoromethyl-1,8-naphthyridin-4(1H)-one

生成物 1

HCID 116204162-anilino-7-[2-(2-oxo-1-pyrrolidinyl)ethoxy]-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one収率 64%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

NaH (60% dispersion, 20.0 mg, 0.514 mmol) was added to a cooled (0° C.) and stirred solution of 1-(2-hydroxyethyl)-2-pyrrolidinone (0.06 mL, 0.514 mmol) in DMF. After 0.5 h, 2-anilino-7-chloro-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one (178 mg, 0.428 mmol) was added as a solid in a single portion and the mixture was heated to 130° C. for 48 h. After cooling to room temperature the mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min) provided 2-anilino-7-[2-(2-oxo-1-pyrrolidinyl)ethoxy]-1-phenyl-5-(trifluoromethyl)-1,8-naphthyridin-4(1H)-one (0.047 g, 64%): LCMS RT: 2.40 min, MH+: 509.2. This transformation can be accomplished by using other aprotic solvents such as DMSO, THF and dioxane with temperatures appropriate for these solvents. Commercially available alkoxides can also be used in the absence of base.

後処理

  1. temperaturethe mixture was heated to 130° C. for 48 h
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas quenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min)

出典と根拠

ORDレコード
ord-8f08a2d2bd47451db862b89a6af49331
出典データセット
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06964971B2

反応ノート

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