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

HRID 1178142
ノート
印刷プレビュー

反応式

HRID 1178142 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]([F:31])([F:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[NH:22][N:21]=[C:20]([C:23]([NH:25][CH2:26][C:27]([OH:29])=O)=[O:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:54]1([C:60]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]([F:71])([F:70])[F:69])=[O:61])[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1>CN(C=O)C.O>[O:29]=[C:27]([N:57]1[CH2:58][CH2:59][N:54]([C:60](=[O:61])[C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][C:63]=2[C:68]([F:71])([F:69])[F:70])[CH2:55][CH2:56]1)[CH2:26][NH:25][C:23]([C:20]1[CH:19]=[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11]([F:10])([F:31])[F:30])[NH:22][N:21]=1)=[O:24]
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 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 178525877HCID 178525877、化合物

生成物 1

HCID 178523536
5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
収率 69.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (137 mg, 0.18 mL, 1.06 mmol) was added to a stirred solution of {[5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (95 mg, 0.30 mmol) in DMF (2 mL). HOBT (47 mg, 0.34 mmol) and EDCI (67 mg, 0.34 mmol) were then added at room temperature. After 2 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (90 mg, 0.30 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 115 mg (68.45% yield) of 5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 93.52%. 1H NMR (DMSO-d6): δ 13.6 (m, 1H), 8.2 (m, 1H), 7.7 (m, 4H), 7.6 (m, 3H), 7.5 (m, 1H), 6.7 (m, 1H), 4.2 (d, 2H), 3.7 (m, 1H), 3.5 (m, 3H), 3.4 (m, 2H), 3.0 (m, 2H).

後処理

  1. filtrationfiltered the solid
  2. customprecipitated out

出典と根拠

ORDレコード
ord-8ff5cad1beb848468ba1459114e0f659
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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