Cyclobutanecarboxylic acid → N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclobutanecarboxamide

HRID 520296Notes

Reaction equation

HRID 520296 reaction equation
[CH:1]1([C:5]([OH:7])=O)[CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:41][C:42]1[C:43](=[O:50])[N:44]([CH3:49])[CH:45]=[C:46]([Br:48])[CH:47]=1>C(Cl)Cl>[Br:48][C:46]1[CH:47]=[C:42]([NH:41][C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)=[O:7])[C:43](=[O:50])[N:44]([CH3:49])[CH:45]=1

Participants

6

Reactant 4

HCID 19494Cyclobutanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 117777382N-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)cyclobutanecarboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture or cyclobutanecarboxylic acid (200 mg, 2.0 mmol), HATU (1.14 g, 3.0 mmol) and DIPEA (516 mg, 4.0 mmol) in DCM (8 mL) was added 3-amino-5-bromo-1-methylpyridin-2(1H)-one (330 mg, 1.62 mmol). The reaction mixture was stirred at 25° C. for 5 hours. The resulting mixture was evaporated under reduced pressure and the residue was purified on a silica-gel column eluting with 20:1 DCM/methanol to afford 101a (230 mg, 54%). MS-ESI: [M+H]+ 285.1

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. customthe residue was purified on a silica-gel column
  3. washeluting with 20:1 DCM/methanol

Sources & evidence

ORD record
ord-d77f39abfd45434e9bb9cbd64d4bf720
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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