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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(2-Fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1178128
ノート
印刷プレビュー

反応式

HRID 1178128 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[O:21][N:20]=[C:19]([C:22]([OH:24])=O)[CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:69])[C:58]2[CH:63]=[C:62]([F:64])[CH:61]=[CH:60][C:59]=2[C:65]([F:68])([F:67])[F:66])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[F:64][C:62]1[CH:61]=[CH:60][C:59]([C:65]([F:67])([F:66])[F:68])=[C:58]([CH:63]=1)[C:57]([N:54]1[CH2:55][CH2:56][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:22]([C:19]2[CH:18]=[C:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[F:10])[O:21][N:20]=2)=[O:24])[CH2:52][CH2:53]1)=[O:69]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167823945-(2-Fluorophenyl)-1,2-oxazole-3-carboxylic acidHCID 669531292-Amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]ethanone hydrochloride

生成物 1

HCID 59559633
5-(2-Fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide
収率 32.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (219 mg, 0.29 mL, 1.68 mmol) was added to a stirred solution of 5-(2-fluoro-phenyl)-isoxazole-3-carboxylic acid (100 mg, 0.48 mmol) in DMF (2 mL). HOBT (68.5 mg, 0.5 mmol) and EDCI (97.2 mg, 0.5 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (100 mg, 0.48 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated. The obtained solid was purified by column chromatography (using silica gel of 60-120 mesh and 50% EtOAc in hexane as eluent) to afford 82 mg (32.5% yield) of 5-(2-fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 98.05%. 1H NMR (DMSO-d6): δ 8.8 (t, 1H), 7.9 (m, 2H), 7.4 (m, 5H), 7.2 (d, 1H), 7.2 (d, 1H), 4.2 (m, 2H), 3.9 (m, 1H), 3.5 (m, 3H), 3.4 (m, 1H), 3.1 (m, 2H).

後処理

  1. filtrationfiltered the solid
  2. customprecipitated
  3. customThe obtained solid was purified by column chromatography (using silica gel of 60-120 mesh and 50% EtOAc in hexane as eluent)

出典と根拠

ORDレコード
ord-d9cc55adffd544cb920f391705d3757b
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842696B2

反応ノート

読み込み中…

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