1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide

HRID 1177883노트

반응식

HRID 1177883 반응식
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH:13]=[N:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[O:50]=[C:49]([N:51]1[CH2:52][CH2:53][N:54]([C:57](=[O:68])[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=2[C:64]([F:67])([F:66])[F:65])[CH2:55][CH2:56]1)[CH2:48][NH:47][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([C:14]2[CH:13]=[N:12][CH:11]=[N:10][CH:15]=2)=[CH:24][CH:23]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 41872474-(Pyrimidin-5-yl)benzoic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

생성물 1

HCID 59559651N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide수율 31.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (185 mg, 0.24 mL, 1.1 mmol) was added to a stirred solution of 4-pyrimidin-5-yl-benzoic acid (85 mg, 0.42 mmol) in DMF (2 mL). HOBT (75 mg, 0.46 mmol) and EDCI (98 mg, 0.46 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (165 mg, 0.46 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent) to afford 65 mg (31% yield) of N-{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-4-pyrimidin-5-yl-benzamide. LCMS Purity: 97%. 1H NMR (CDCl3): δ 9.2 (s, 1H), 9.0 (s, 2H), 8.0 (dd, 2H), 7.56 (d, 1H), 7.65 (m, 4H), 7.35 (m, 2H), 4.35 (m, 1H), 4.25 (m, 1H), 4.0 (m, 2H), 3.7 (m, 2H), 3.6 (m, 2H), 3.42 (m, 1H), 3.25 (m, 2H).

후처리

  1. filtrationfiltered the residue
  2. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent)

출처 및 근거

ORD 기록
ord-22f63a14c08a43ea99c83443959fe478
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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