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

HRID 1177917
ノート
印刷プレビュー

反応式

HRID 1177917 の反応式
CCN(C(C)C)C(C)C.Cl.[NH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])[CH2:17][CH2:16]1)=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:54][C:55]1[N:59]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[N:58]=[CH:57][C:56]=1[C:66](O)=[O:67]>CN(C=O)C.O>[O:14]=[C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:29])[F:30])[CH2:19][CH2:20]1)[CH2:12][NH:11][C:66]([C:56]1[CH:57]=[N:58][N:59]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C:55]=1[CH3:54])=[O:67]
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 1452215-Methyl-1-phenylpyrazole-4-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

生成物 1

HCID 25166501
5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
収率 11.74%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (189 mg, 0.256 mL, 1.48 mmol) was added to a stirred solution of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above) (208 mg, 0.59 mmol) in DMF (2 mL). HOBT (80 mg, 0.59 mmol) and EDCI (114 mg, 0.59 mmol) were then added at room temperature. After 2 minutes, 5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid (100 mg, 0.49 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 29 mg (11.74% yield) 5-Methyl-1-phenyl-1H-pyrazole-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 94.32%. 1H NMR (DMSO-d6): δ 8.24 (bs, 1H), 8.14 (s, 1H), 7.88-7.74 (m, 2H), 7.7-7.6 (m, 1H), 7.6-7.4 (m, 6H), 4.2-4.4 (d, 2H), 3.9-3.6 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.0 (m, 2H).

後処理

  1. customprepared by the method
  2. extractionthe product was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-60da7f74c019458ab7b4b6233c7cc6dd
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

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