Acetonitrile → HCID 46928271, compound

HRID 1645313Notes

Reaction equation

HRID 1645313 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:23][O:24][C@@H:25]1[C@@H:29]([NH:30][CH3:31])[CH2:28][NH:27][CH2:26]1.C(#N)C.[CH2:35]([O:37][C:38]([C:40]1[C:49](=[O:50])[C:48]2[C:43](=[N:44][C:45](Cl)=[CH:46][CH:47]=2)[N:42]([C:52]2[S:53][CH:54]=[CH:55][N:56]=2)[CH:41]=1)=[O:39])[CH3:36]>[Ag].C(N(CC)CC)C>[CH3:23][O:24][C@@H:25]1[C@@H:29]([NH:30][CH3:31])[CH2:28][N:27]([C:45]2[N:44]=[C:43]3[C:48]([C:49](=[O:50])[C:40]([C:38]([O:37][CH2:35][CH3:36])=[O:39])=[CH:41][N:42]3[C:52]3[S:53][CH:54]=[CH:55][N:56]=3)=[CH:47][CH:46]=2)[CH2:26]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 46928269HCID 46928269, compoundHCID 46928270Ethyl 7-chloro-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 46928271HCID 46928271, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 8471TriethylamineSolvent

Procedure

To a glass reactor covered with silver foil and equipped with an overhead stirrer was added (3S,4S)-3-methoxy-4-methylaminopyrrolidine di-p-toluenesulfonic acid (1190 g) and acetonitrile (9.0 L), and the mixture stirred. The solution was cooled and triethylamine (TEA) (1560 mL) was added, maintaining the batch temperature below 5° C. Ethyl-7-chloro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylate (750 g) was added, the ice-bath was removed and the reaction temperature allowed to rise and then stirred an additional 48 hours. The reaction was filtered, the filter cake was washed with acetonitrile (3×800 mL), and dried in vacuo to afford 936 g of the title compound as a white solid (97.6%).

Workup

  1. customequipped with an overhead stirrer
  2. temperatureThe solution was cooled
  3. temperaturemaintaining the batch temperature below 5° C
  4. customthe ice-bath was removed
  5. stirringstirred an additional 48 hours
  6. filtrationThe reaction was filtered
  7. washthe filter cake was washed with acetonitrile (3×800 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f9046cc316b04f9e868965b756da23ad
Source dataset
uspto-grants-2012_02
Patent number
US08124773B2

Reaction notes

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