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 1177876노트

반응식

HRID 1177876 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4d3fc93e2c5431ca700205830c5be94
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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