1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramide

HRID 2357887Notes

Reaction equation

HRID 2357887 reaction equation
[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.[C:57]1([CH2:63]CCN)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:57]1([CH2:63][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:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162593-PhenylpropylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 67419145[4-(6-Aminopyridin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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), EDCI (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).

Workup

  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

Sources & evidence

ORD record
ord-33d519993d864d029b041a1290daf27d
Source dataset
uspto-grants-2010_07
Patent number
US07763618B2

Reaction notes

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