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

HRID 1093844
ノート
印刷プレビュー

反応式

HRID 1093844 の反応式
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:49][C:50]([F:64])([F:63])[C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]1[CH2:59][CH2:58][NH:57][CH2:56]1>CN(C=O)C.O>[O:27]=[C:25]([N:57]1[CH2:58][CH2:59][CH:55]([O:54][C:53]2[CH:60]=[CH:61][CH:62]=[C:51]([C:50]([F:49])([F:64])[F:63])[CH:52]=2)[CH2:56]1)[CH2:24][NH:23][C:21]([C:18]1[CH:17]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:20][N:19]=1)=[O:22]
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 183371713-[3-(Trifluoromethyl)phenoxy]pyrrolidineHCID 178525878HCID 178525878、化合物

生成物 1

HCID 178523504
5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-ethyl}-amide
収率 61.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (167.7 mg, 1.29 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (106 mg, 0.43 mmol) in DMF (4 mL) followed by HOBt (70.13 mg, 0.52 mmol) and EDCI (99.5 mg, 0.52 mmol). After 2 minutes of stirring, 3-(3-trifluoromethyl-phenoxy)-pyrrolidine (100 mg, 0.43 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected to afford 122 mg (61.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 459.16, 96.52%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (s, 1H), 8.05 (bs, 1H), 7.8 (db, 2H), 7.7-7.6 (m, 7H), 7.05 (bs, 1H), 5.4 (s, 1H), 5.3 (s, 1H), 4.1 (m, 2H), 3.9 (m, 1H), 3.8-3.6 (m, 3H), 3.4 (m, 1H), 2.3-2.0 (m, 2H).

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customthe precipitate was collected

出典と根拠

ORDレコード
ord-1ab4f5c258b4430ea58c672f585354b9
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129376B2

反応ノート

読み込み中…

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