Citric Acid → HCID 59696343, compound

HRID 2075287Notes

Reaction equation

HRID 2075287 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:11]=[N:12]2)=[C:7]([I:24])[N:6]=1)=[O:4].C1CCN2C(=NCCC2)CC1.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.S([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:11]=[N:12]2)=[C:7]([I:24])[N:6]=1)=[O:4]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23665763Sodium BisulfiteHCID 59696499HCID 59696499, compound

Product 1

HCID 59696343HCID 59696343, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide suspension (80 ml) of the above Compound 7 (8.76 g, 20 mmol) were added DBU (4.48 ml, 30 mmol) and benzylbromide (3.56 ml, 30 mmol), and the solution was stirred for 5 hours at room temperature. The reaction solution was added with 0.5M citric acid aqueous solution and 10% sodium hydrogen sulfite aqueous solution, and extracted twice with ethyl acetate. The organic phase was washed with water, saturated sodium hydrogen carbonate and saturated brine. After drying over anhydrous magnesium sulfate, the residue obtained by distilling off the solvent was subjected to silica gel chromatography. The precipitated crystals were collected by filtering, and washed with diisopropyl ether, to give 8-benzyloxy-3-(4-fluorobenzyl)-5-iodo[1,6]naphthyridine-7-carboxylic acid methyl ester 8 (7.64 g) in 72% yield.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phase was washed with water, saturated sodium hydrogen carbonate and saturated brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. customthe residue obtained
  5. distillationby distilling off the solvent
  6. customThe precipitated crystals were collected
  7. filtrationby filtering
  8. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-a143ea7763ec40e2a39d18825df6cfda
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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