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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
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HRID 1063549 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8f08a2d2bd47451db862b89a6af49331
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06964971B2

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