Hydrochloric Acid → HCID 178462515, compound

HRID 2293973Notes

Reaction equation

HRID 2293973 reaction equation
[C:1]([C:3]1[C:12](=[O:13])[C:11]2[C:6](=[C:7]([O:27][CH:28]([F:30])[F:29])[C:8]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[N:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[C:9]([F:14])[CH:10]=2)[N:5]([CH2:31][CH3:32])[CH:4]=1)#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC.Cl>C1(C)C(C)=CC=CC=1>[CH2:31]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([F:14])=[C:8]([N:15]3[CH2:16][CH2:17][N:18]([C:21]4[N:22]=[CH:23][CH:24]=[CH:25][N:26]=4)[CH2:19][CH2:20]3)[C:7]=2[O:27][CH:28]([F:30])[F:29])[C:12](=[O:13])[C:3]([C:1]2[NH:35][N:34]=[N:33][N:2]=2)=[CH:4]1)[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 21473368HCID 21473368, compound

Product 1

HCID 178462515HCID 178462515, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 25 ml of xylene were added 0.5 g (0.0011 mole) of 3-cyano-1-ethyl-6-fluoro-8-difluoromethoxy-7-[4-(2-pyrimidinyl)piperazin-1-yl]-1,4-dihydro-4-oxoquinoline obtained as described above, 0.21 g of (0.0033 mole) of sodium azide and 1.07 g (0.0033 mole) of tributyltin chloride, and the mixture was stirred under reflux by heating for 9 hours. After the mixture was cooled to room temperature, 7 ml of a 1N hydrochloric acid aqueous solution was added thereto, and the mixture was stirred. Then, crystals precipitated were collected by filtration, washed with ethanol and toluene, and applied to silica gel column chromatography (the eluent used was a mixture of chloroform:methanol=9:1) to obtain 0.37 g of the title compound as pale yellow powder.

Workup

  1. customobtained
  2. temperatureunder reflux
  3. temperatureby heating for 9 hours
  4. stirringthe mixture was stirred
  5. customThen, crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with ethanol and toluene
  8. additiona mixture of chloroform

Sources & evidence

ORD record
ord-0f1cf3a603464d8eb66f0dab6d93b774
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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