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

HRID 1665693Notes

Reaction equation

HRID 1665693 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([N:49]2[CH:53]=[C:52]([NH2:54])[CH:51]=[N:50]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:54][C:52]2[CH:51]=[N:50][N:49]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:53]=2)=[O:16])[CH2:10][CH2:11]1)=[O:5]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1210211-Phenyl-1H-pyrazol-4-amineHCID 578758013-[4-(2-Bromo-benzoyl)-piperazin-1-yl]-3-oxo-propionic acid

Product 1

HCID 442317983-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(1-phenyl-1H-pyrazol-4-yl)-propionamideYield 36%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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, 1-phenyl-1H-pyrazol-4-ylamine (54 mg, 0.33 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford 50 mg (35.97% yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(1-phenyl-1H-pyrazol-4-yl)-propionamide. LC/MS [M+H]+: 596.09, 87.79%. 1H NMR (300 MHz, DMSO-d6): δ 10.4 (d, 1H), 8.5 (d, 1H), 7.84-7.64 (m, 4H), 7.54-7.2 (m, 5H), 4.0-3.8 (m, 7H), 3.2-3.1 (m, 2H).

Workup

  1. waitwas continued at room temperature overnight
  2. extractionthe mixture 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-4aca82d7ced84402a0552639f935801f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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