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

HRID 1177995

반응식

HRID 1177995 반응식
CCN(C(C)C)C(C)C.[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=[CH:14][C:13]([C:16]([N:18]([CH2:20][C:21]([OH:23])=O)[CH3:19])=[O:17])=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:52]1([C:58]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])=[O:59])[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>CN(C=O)C.O>[CH3:19][N:18]([CH2:20][C:21](=[O:23])[N:55]1[CH2:56][CH2:57][N:52]([C:58](=[O:59])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:67])[F:68])[CH2:53][CH2:54]1)[C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1)=[O:17]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 43239699[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid

생성물 1

HCID 59559638Biphenyl-4-carboxylic acid methyl-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide수율 71.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (216 mg, 0.3 mL, 1.6 mmol) was added to a stirred solution of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid (100 mg, 0.37 mmol) in DMF (3 mL). HOBT (55.2 mg, 0.4 mmol) and EDCI (178 mg, 0.92 mmol) were then added at room temperature. After 2 minutes piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (131 mg, 0.44 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 135 mg (71.3% yield) of biphenyl-4-carboxylic acid methyl-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 96.56%. 1H NMR (DMSO-d6): δ 7.9-7.6 (m, 7H), 7.6-7.45 (q, 4H), δ 7.45-7.3 (q, 2H), 4.5-4.2 (m, 2H), 4.15 (s, 1H), 3.8-3.5 (m, 4H), 3.5-3.4 (m, 2H), 3.25-3.1 (m, 2H), 3.0 (s, 3H).

후처리

  1. filtrationfiltered the solid
  2. customprecipitated out

출처 및 근거

ORD 기록
ord-2f25f3de09f14ad99655326ba4f5b2ca
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

연결된 노트

불러오는 중…