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Ethyl Thioglycolate → Ethyl {[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]sulfanyl}acetate

HRID 1063546
ノート
印刷プレビュー

反応式

HRID 1063546 の反応式
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:10]([C:17]1[N:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]2[C:24]([C:25](=[O:27])[CH:26]=1)=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=[C:21](Cl)[N:20]=2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C>[NH:10]([C:17]1[N:18]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]2[N:20]=[C:21]([S:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:22]=[C:23]([C:28]([F:31])([F:30])[F:29])[C:24]=2[C:25](=[O:27])[CH:26]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=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 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 219481692-anilino-7-chloro-1-phenyl-5-trifluoromethyl-1,8-naphthyridin-4(1H)-one

生成物 1

HCID 11684737Ethyl {[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]sulfanyl}acetate収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

NaH (60% dispersion in oil, 18.0 mg, 0.434 mmol) was added to a cooled (0° C.) and stirred solution of ethyl mercaptoacetate (0.05 mL, 0.434 mmol) in DMF. After 0.5 h, 2-anilino-7-chloro-1-phenyl-5-trifluoromethyl-1,8-naphthyridin-4(1H)-one (150.0 mg, 0.361 mmol) was added as a solid in a single portion. The mixture was allowed to warm to room temperature and was stirred for 24 h. The reaction was quenched with water 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 ethyl {[7-anilino-5-oxo-8-phenyl-4-(trifluoromethyl)-5,8-dihydro-1,8-naphthyridin-2-yl]sulfanyl}acetate (50 mg, 53%): LCMS RT: 3.91 min, MH+: 500.2, Rf=0.24 (1:1 EtOAc:Hex).

後処理

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. 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-15a6d091ede447eabbda7fc57b734a12
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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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