Cyclopropanecarboxylic acid → HCID 117777391, compound

HRID 520298Notes

Reaction equation

HRID 520298 reaction equation
[CH:1]1([C:4]([OH:6])=O)[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.[NH2:40][C:41]1[C:42](=[O:49])[N:43]([CH3:48])[CH:44]=[C:45]([Br:47])[CH:46]=1>C(Cl)Cl>[Br:47][C:45]1[CH:46]=[C:41]([NH:40][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:6])[C:42](=[O:49])[N:43]([CH3:48])[CH:44]=1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic 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 117777391HCID 117777391, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of cyclopropanecarboxylic acid (180 mg, 2.0 mmol), HATU (570 mg, 1.5 mmol) and DIPEA (390 mg, 3.0 mmol) in DCM (8 mL) was added 3-amino-5-bromo-1-methylpyridin-2(1H)-one (230 mg, 1.12 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 chromatography eluting with 20:1 DCM/methanol to afford the 102a (220 mg, 72%). MS-ESI: [M+H]+ 270.1

Workup

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

Sources & evidence

ORD record
ord-0c50b0439d7d4f13ad1bf8230a04b2f0
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

Loading…