Hydrochloric Acid → HCID 23149774, compound

HRID 2075288Notes

Reaction equation

HRID 2075288 reaction equation
C[O:2][C:3]([C:5]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]2[C:8]([CH:9]=[C:10]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:11]=[N:12]2)=[C:7]([I:31])[N:6]=1)=[O:4].O1CCCC1.[OH-].[Na+].Cl>CO>[CH2:16]([O:15][C:14]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([I:31])=[C:8]2[C:13]=1[N:12]=[CH:11][C:10]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[CH:9]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59696343HCID 59696343, compound

Product 1

HCID 23149774HCID 23149774, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the above Compound 8 (20.0 g, 37.86 mmol) was added tetrahydrofuran (100 ml) and methanol (100 ml) to give suspension, followed by addition of 2N sodium hydroxide aqueous solution (24.6 ml, 49.2 mmol) under stirring at room temperature and stirring was continued. After 4 hours, 2N hydrochloric acid (24.6 ml, 49.2 mmol) was added, and the reaction solution was concentrated under reduced pressure and added with chloroform (150 ml) and water (150 ml). Then the solution was shaken for separation, washed with saturated sodium hydrogen carbonate and dried over sodium sulfate, followed by distillation under reduced pressure. The residue (20.8 g) was added with diisopropyl ether (80 ml) and n-hexane (80 ml), warmed on a water bath for crystallization, and then the crystals were collected by filtering and washed with diisopropyl ether:n-hexane (1:1), to give 8-benzyloxy-3-(4-fluorobenzyl)-5-iodo[1,6]naphthyridine-7-carboxylic acid 9 in a yield of (19.41 g, 99.7%).

Workup

  1. customto give suspension
  2. stirringstirring
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionadded with chloroform (150 ml) and water (150 ml)
  5. stirringThen the solution was shaken for separation
  6. washwashed with saturated sodium hydrogen carbonate
  7. dry with materialdried over sodium sulfate
  8. distillationfollowed by distillation under reduced pressure
  9. additionThe residue (20.8 g) was added with diisopropyl ether (80 ml) and n-hexane (80 ml)
  10. temperaturewarmed on a water bath for crystallization
  11. customthe crystals were collected
  12. filtrationby filtering
  13. washwashed with diisopropyl ether:n-hexane (1:1)

Sources & evidence

ORD record
ord-1a35f9d32d8c44b7af10cba292bb7fcc
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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