Triethylamine → HCID 66725402, compound

HRID 1888800Notes

Reaction equation

HRID 1888800 reaction equation
I[C:2]1[CH:3]=[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].[C:34](=[N:37][OH:38])([NH2:36])[CH3:35].[CH2:39](N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:33][S:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][NH:22][C:20]([C:4]2[C:5](=[O:19])[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=3)[C:7]([CH3:8])=[C:2]([C:39]3[O:38][N:37]=[C:34]([CH3:35])[N:36]=3)[CH:3]=2)=[O:21])=[CH:29][CH:28]=1)(=[O:31])=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 30926N-HydroxyacetamidineHCID 115199335-Iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoro-methyl)phenyl]1,2-dihydropyridine-3-carboxamide

Product 1

HCID 66725402HCID 66725402, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

5-Iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (0.236 g, 0.4 mmol), acetamide oxime (0.088 g, 1.2 mmol), Pd(PPh3)2Cl2 (0.014 g, 0.020 mmol), triethylamine (0.081 g, 0.8 mmol), toluene (15 ml) and a magnetic stirrer bar were loaded into a pressure safe steel reactor. The reactor was degassed with CO, and when all air had been removed, a 4 atmospheres pressure of CO was applied, and the reactor was heated to 95° C. The reaction was allowed to proceed overnight. LC-MS showed that almost all starting iodide had been consumed to give a main product. The crude mixture was evaporated and the residual oil was partitioned between EtOAc and water. The organic phase was collected, and was dried and evaporated. Purification on silica (heptane:EtOAc 1:2) gave pure material (0.083 g, 38%) as a white solid.

Workup

  1. customThe reactor was degassed with CO, and when all air
  2. customhad been removed
  3. customhad been consumed
  4. customto give a main product
  5. customThe crude mixture was evaporated
  6. customthe residual oil was partitioned between EtOAc and water
  7. customThe organic phase was collected
  8. customwas dried
  9. customevaporated
  10. customPurification on silica (heptane:EtOAc 1:2)

Sources & evidence

ORD record
ord-9265dc59d0a748389643a9bf97e692fc
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

Loading…