1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177876ノート

反応式

HRID 1177876 の反応式
CCN(C(C)C)C(C)C.[C:10]1([CH2:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]([OH:28])=O)[CH2:22][CH2:21]2)=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:57][CH2:58][C:59]([N:61]1[CH2:66][CH2:65][N:64]([C:67](=[O:78])[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=2[C:74]([F:77])([F:76])[F:75])[CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.O>[O:60]=[C:59]([N:61]1[CH2:62][CH2:63][N:64]([C:67](=[O:78])[C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=2[C:74]([F:77])([F:76])[F:75])[CH2:65][CH2:66]1)[CH2:58][NH:57][C:26]([CH:23]1[CH2:22][CH2:21][N:20]([C:18](=[O:19])[CH2:17][CH2:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:25][CH2:24]1)=[O:28]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28131931-(3-Phenylpropanoyl)piperidine-4-carboxylic acidHCID 866340882-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone TFA salt

生成物 1

HCID 595595781-(3-Phenyl-propionyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide収率 27.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (72.27 mg, 0.09 mL, 0.55 mmol) was added to a stirred solution of 1-(3-phenyl-propionyl)-piperidine-4-carboxylic acid (58.38 mg, 0.22 mmol) in DMF (1 mL). HOBT (30.2 mg, 0.22 mmol) and EDCI (42.76 mg, 0.22 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (80 mg, 0.18 mmol) was added and the resulting mixture was stirred at room temperature for 16 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 28 mg (26.89% yield) of 1-(3-phenyl-propionyl)-piperidine-4-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide, LCMS Purity: 92.41%. 1H NMR (CDCl3): δ 7.8-7.7 (d, 1H), 7.68-7.52 (m, 2H), 7.38-7.28 (m, 2H), 7.26-7.14 (m, 3H), 6.62-6.48 (s, 1H), 4.7-4.55 (d, 1H), 4.2-3.4 (m, 9H), 3.4-3.1 (d, 3H), 3.05-2.85 (t, 3H), 2.7-2.5 (t, 3H), 2.5-2.3 (t, 2H), 1.9-1.3 (t, 2H), 0.9 (d, 1H).

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-c4d3fc93e2c5431ca700205830c5be94
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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