4-Methylmorpholine → N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-(3-isopropyl-2,5-dioxo-piperazin-1-yl)-acetamide

HRID 2039010Notes

Reaction equation

HRID 2039010 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:50])[CH2:33][NH:34][C:35]([CH2:37][NH:38][CH2:39][C:40]([NH:42][CH:43]([CH:47]([CH3:49])[CH3:48])[C:44](O)=[O:45])=[O:41])=[O:36])=[CH:28][CH:27]=1.CN1CCOCC1>CN(C=O)C>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:50])[CH2:33][NH:34][C:35](=[O:36])[CH2:37][N:38]2[CH2:39][C:40](=[O:41])[NH:42][CH:43]([CH:47]([CH3:49])[CH3:48])[C:44]2=[O:45])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666200532-[2-({[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-methyl]-amino)-acetylamino]-3-methyl-butyric acid

Product 1

HCID 66620101N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-(3-isopropyl-2,5-dioxo-piperazin-1-yl)-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (3.70 g, 9.7 mmol) was added to a solution of 2-[2-({[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-methyl}-amino)-acetylamino]-3-methyl-butyric acid (2.78 g, 6.5 mmol), and 4-methylmorpholine (3.57 mL, 32.5 mmol) in DMF (100 mL). After 30 min the solvent was removed under reduced pressure. The residue was taken up in dichloromethane (150 mL) and washed with water (50 mL), aqueous hydrogen chloride (0.5 N, 2×50 mL), saturated sodium bicarbonate (50 mL) and dried over sodium sulfate. The mixture was filtered and the solvent was removed under reduced pressure. The residue was subjected to flash chromatography with eluent of (10% methanol in ethyl acetate) and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to yield N-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-(3-isopropyl-2,5-dioxo-piperazin-1-yl)-acetamide (1.56 g, 3.8 mmol, 60%). C17H20BrN3O4 calculated 409.1 observed [M+1]+ 410.1; rt=2.00 min.

Workup

  1. customAfter 30 min the solvent was removed under reduced pressure
  2. washwashed with water (50 mL), aqueous hydrogen chloride (0.5 N, 2×50 mL), saturated sodium bicarbonate (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvent was removed under reduced pressure
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1fb907de6ca148768b30d2c4c474f390
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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