1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(4-pyridin-3-yl-phenyl)-propionamide

HRID 1665690노트

반응식

HRID 1665690 반응식
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:17])[CH2:13][C:14]([OH:16])=O)[CH2:8][CH2:7]1)=[O:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]2[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=2)[CH:44]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:17])[CH2:13][C:14]([NH:55][C:52]2[CH:51]=[CH:50][C:49]([C:45]3[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=3)=[CH:54][CH:53]=2)=[O:16])[CH2:10][CH2:11]1)=[O:5]

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4595224-(Pyridin-3-yl)anilineHCID 578758013-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

생성물 1

HCID 442317973-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(4-pyridin-3-yl-phenyl)-propionamide수율 60.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DMAP (68 mg, 0.56 mmol) was added to 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid (100 mg, 0.28 mmol) in DMF (2 mL) followed by EDCI (64 mg, 0.33 mmol) and HOBT (45 mg, 0.33 mmol). After 2 minutes, 4-pyridin-3-yl-phenylamine (55 mg, 0.18 mmol) was added and it was stirred at room temperature overnight. Cold water was then added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 55 mg (38.73% yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(4-pyridin-3-yl-phenyl)-propionamide. LC/MS [M+H]+: 507.1, 90.55%. 1H NMR (300 MHz, DMSO-d6): δ 10.25 (d, 1H), 8.9 (bt, 1H), 8.5 (d, 1H), 8.1-8.0 (m, 1H), 7.7 (d, 5H), 7.52-7.3 (m, 4H), 3.8-3.46 (m, 8H), 3.2 (bt, 1H), 3.1 (bt, 1H).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-487aaaf2dfd34b1184c77033f2f997da
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039463B2

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