1-Hydroxybenzotriazole → N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-2-methyl-3-oxo-propionamide

HRID 1665677노트

반응식

HRID 1665677 반응식
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.Cl.[Br:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)=[O:41].[C:48]1([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[CH:53]=[CH:52][C:51]([NH:54][C:55](=[O:61])[CH:56]([CH3:60])[C:57](O)=[O:58])=[CH:50][CH:49]=1>CN(C=O)C.O>[C:48]1([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:53]=[CH:52][C:51]([NH:54][C:55](=[O:61])[CH:56]([CH3:60])[C:57]([N:45]2[CH2:44][CH2:43][N:42]([C:40](=[O:41])[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[Br:33])[CH2:47][CH2:46]2)=[O:58])=[CH:50][CH:49]=1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57875794N-biphenyl-4-yl-2-methyl-malonamic acidHCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

생성물 1

HCID 44231681N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-2-methyl-3-oxo-propionamide수율 73%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

HOBt (60 mg, 0.44 mmol), DIPEA (140 mg, 1.1 mmol), EDCI.HCl (85 mg, 0.44 mmol) followed by (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (136 mg, 0.44 mmol), were added to a stirred solution of N-biphenyl-4-yl-2-methyl-malonamic acid (100 mg, 0.37 mmol) in DMF (2.0 mL). The resulting mixture was stirred at ambient temperature overnight then diluted with water. The product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and concentrated under reduced pressure to afford 140 mg (73%) of N-biphenyl-4-yl-3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-2-methyl-3-oxo-propionamide. LCMS: 520.12 (M+1)+, 97.32%, 1H NMR (DMSO-d6): δ 10.2 (d, 1H), 7.8-7.3 (m, 13H), 4.0-3.4 (m, 7H), 3.2-3.0 (m, 2H), 1.3 (m, 3H).

후처리

  1. extractionThe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4a600e8a4f1a4b0cabceebb5b2e4653b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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