1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-3-methyl piperazin-2-one

HRID 467543ノート

反応式

HRID 467543 の反応式
C(N(CC)C(C)C)(C)C.[CH3:10][CH:11]1[NH:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([O:59]C)[CH:42]=1)[CH3:40]>ClCCl.O>[CH2:39]([C:41]1[C:57]([F:58])=[CH:56][C:44]([O:45][C:46]2[CH:54]=[CH:53][C:49]([C:50]([N:16]3[CH2:15][CH2:14][NH:13][C:12](=[O:17])[CH:11]3[CH3:10])=[O:51])=[CH:48][C:47]=2[F:55])=[C:43]([OH:59])[CH:42]=1)[CH3:40]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 51066003-Methyl-2-ketopiperazineHCID 671160464-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid

生成物 1

HCID 513567694-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]-3-methyl piperazin-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

N,N-Diisopropylethylamine (74 μL, 0.42 mmol), 3-methylpiperazin-2-one (23.3 mg, 0.20 mmol), EDCI (39.1 mg, 0.20 mmol) and HOBt (27.6 g, 0.20 mmol) were successively added to a suspension of 4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoic acid (which may be prepared in accordance with the experimental described in Example 4, step 4; 50 mg, 0.17 mmol) in dichloromethane (0.55 mL). The reaction mixture was stirred at room temperature overnight then diluted by addition of dichloromethane (10 mL) and water (10 mL). After separation, the organic layer was washed with water (10 mL). The organic phase was dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (98:2 to 95:5) as eluent. The title product was obtained as a white solid (24 mg, 36%).

後処理

  1. custommay be prepared in accordance with the
  2. customAfter separation
  3. washthe organic layer was washed with water (10 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-38d5c65b873240e484ceb314d129b9d6
出典データセット
uspto-grants-2014_01
特許番号
US08623865B2

反応ノート

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