Dimethylformamide → (5-Bromo-thiophen-2-yl)-{[1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-acetic acid methyl ester

HRID 1625477Notes

Reaction equation

HRID 1625477 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:10][C:11]([C:13]1[C:14](=[O:28])[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:12])[C:5]1[S:6][CH:7]=[CH:8][CH:9]=1.CN(C)C=O.[Br:35]N1C(=O)CCC1=O>>[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:5]1[S:6][C:7]([Br:35])=[CH:8][CH:9]=1)[NH:10][C:11]([C:13]1[C:14](=[O:28])[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 68610280{[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-thiophen-2-yl-acetic acid methyl ester

Product 1

HCID 68607555(5-Bromo-thiophen-2-yl)-{[1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-acetic acid methyl ester

Procedure

{[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-thiophen-2-yl-acetic acid methyl ester (0.190 g, 0.000454 mol;) was dissolved in N,N-Dimethylformamide (6 mL, 0.07 mol;) and N-Bromosuccinimide (0.089 g, 0.00050 mol;) was added. The reaction was allowed to stir at room temperature o/n. LC-MS showed the formation of product at 1.89 498.45. The reaction was concentrated and dissolved in ethyl acetate. The reaction was then washed 1× with saturated bicarbonate and 1× with brine before drying with magnesium sulfate and concentrating. The crude was then dissolved in methylene chloride and injected onto the combiflash and eluted using a 0-100% hexanes ethyl acetate gradient. The pure fractions were combined and concentrated to give the product. ES (+) MS m/e=498.45

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washThe reaction was then washed 1× with saturated bicarbonate and 1× with brine
  4. dry with materialbefore drying with magnesium sulfate
  5. concentrationconcentrating
  6. dissolutionThe crude was then dissolved in methylene chloride
  7. washeluted
  8. concentrationconcentrated
  9. customto give the product

Sources & evidence

ORD record
ord-7c1b32dc42614930ac3addce13df35f3
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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