1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide

HRID 1665698Notes

Reaction equation

HRID 1665698 reaction equation
[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.[C:43]1([C:49]2[CH:50]=[CH:51][C:52]([NH2:55])=[N:53][CH:54]=2)[CH:48]=[CH:47][CH:46]=[CH:45][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:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:54][N:53]=2)=[O:16])[CH2:10][CH2:11]1)=[O:5]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1050975-Phenyl-2-pyridinamineHCID 578758013-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

Product 1

HCID 578758043-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamideYield 27.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DMAP (137 mg, 1.1 mmol) was added to 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid (200 mg, 0.56 mmol) in DMF (2 mL) followed by EDCI (129 mg, 0.67 mmol) and HOBT (91 mg, 0.67 mmol). After 2 minutes, 5-phenyl-pyridin-2-ylamine (115 mg, 0.67 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and it was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 77 mg (27% yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(5-phenyl-pyridin-2-yl)-propionamide. LC/MS [M+H]+: 507.1, 97.03%. 1H NMR (300 MHz, DMSO-d6): δ 10.8 (d, 1H), 8.7-8.6 (bs, 1H), 8.2-8.06 (m, 2H), 7.76-7.64 (m, 3H), 7.54-7.34 (m, 6H), 3.8-3.4 (m, 8H), 3.24-3.1 (m, 2H).

Workup

  1. waitwas continued at room temperature overnight
  2. extractionit was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0791615c75564be287c974e56bd6e033
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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