3-Phenylpropylamine → 4-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramide

HRID 389976노트

반응식

HRID 389976 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N([CH:32]([CH3:34])[CH3:33])CC)(C)C.O.[OH:36]N1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[C:58]1([CH2:64]CCN)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:58]1([CH2:64][CH2:34][CH2:32][C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14](=[O:15])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:13]3)=[CH:6][N:7]=2)=[O:36])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

참가 물질

9

반응물 5

HCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67419145[4-(6-Aminopyridin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

생성물 1

HCID 111911704-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramide수율 12.5%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in dichloromethane was added diisopropylethylamine (0.084 mL, 0.48 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.018 g, 0.12 mmol), EDCl (0.023 g, 0.12 mmol) and DMAP (0.015 g, 0.12 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.020 g, 0.12 mmol) was added. After stirring for 18 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a pale white solid (6.2 mg, 12.5% yield). 1H NMR (300 MHz, CDCl3) δ 8.12, 7.97, 7.87, 7.72, 7.59, 7.34, 7.10-7.29, 3.98, 3.34, 3.22, 3.02, 2.70, 2.37, 2.08. MS (ES+) m/z 497.2 (M+1).

후처리

  1. stirringAfter stirring for 18 h
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-0eb8be18f1c644dd936b3733eba66ee7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383628B2

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