Sodium Hydroxide → HCID 178516884, compound

HRID 1094192Notes

Reaction equation

HRID 1094192 reaction equation
O1CCOCC1.[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:33])[C:19]([O:29][CH2:30][C:31]#[N:32])=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:34])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C([Sn]([N:48]=[N+:49]=[N-:50])(CCCC)CCCC)CCC.[OH-].[Na+]>CCOCC>[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:33])[C:19]([O:29][CH2:30][C:31]4[NH:50][N:49]=[N:48][N:32]=4)=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:34])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 4984872Tributyltin azideHCID 66636991HCID 66636991, compound

Product 1

HCID 178516884HCID 178516884, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 5 ml 1,4-dioxane solution of 300 mg of {[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}acetonitrile was added 0.8 ml of tributyltin azide, followed by heating under reflux for 2 days. After cooling to room temperature, aqueous 1M sodium hydroxide solution and ether were added, followed by layer separation operation. To the aqueous layer was added 1 M hydrochloric acid, followed by extraction with chloroform and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure. By adding ether to the resulting residue and collecting the insoluble materials by filtration, 70 mg of 7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-3-(1H-tetrazol-5-ylmethoxy)quinolin-4(1H)-one was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 days
  3. customfollowed by layer separation operation
  4. additionTo the aqueous layer was added 1 M hydrochloric acid
  5. extractionfollowed by extraction with chloroform
  6. washwashing with aqueous saturated sodium chloride
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. additionBy adding ether to the resulting residue
  10. customcollecting the insoluble materials
  11. filtrationby filtration

Sources & evidence

ORD record
ord-bce0019712d64e13a4f302e0b149a128
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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