1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamide

HRID 1177880ノート

反応式

HRID 1177880 の反応式
CCN(C(C)C)C(C)C.[S:10]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)=[CH:11]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:52][CH2:53][C:54]([N:56]1[CH2:61][CH2:60][N:59]([C:62](=[O:73])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])[CH2:58][CH2:57]1)=[O:55]>CN(C=O)C.O>[O:55]=[C:54]([N:56]1[CH2:57][CH2:58][N:59]([C:62](=[O:73])[C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=2[C:69]([F:72])([F:71])[F:70])[CH2:60][CH2:61]1)[CH2:53][NH:52][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][S:10][CH:11]=2)=[CH:23][CH:22]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7368624-(3-Thienyl)benzoic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

生成物 1

HCID 59559628N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamide収率 48.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (74.9 mg, 0.09 mL, 0.58 mmol) was added to a stirred solution of 4-thiophen-3-yl-benzoic acid (40 mg, 0.19 mmol) in DMF (1 mL). HOBT (32 mg, 0.23 mmol) and EDCI (45 mg, 0.23 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (100 mg, 0.23 mmol) was added and the resulting mixture was stirred at room temperature overnight. 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 46 mg (46.9% yield) of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-thiophen-3-yl-benzamide. LCMS Purity: 97.5%. 1H NMR (DMSO-d6): δ 8.7-8.6 (m, 1H), 8.1-8.0 (s, 1H), 7.96-7.9 (m, 2H), 7.88-7.8 (m, 3H), 7.8-7.74 (m, 1H), 7.72-7.62 (m, 3H), 7.6-7.5 (bt, 1H), 4.24-4.08 (m, 2H), 3.78-3.56 (m, 4H), 3.5-3.4 (m, 2H), 3.2-3.06 (m, 2H).

後処理

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

出典と根拠

ORDレコード
ord-0cbea3ab9cff4136b7c49272adcdad17
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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