Boric Acid → HCID 89561379, compound

HRID 1525125Notes

Reaction equation

HRID 1525125 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:17])[C:6]([C:18]([O:20]C(C3C(=O)C4C(=C(OC)C(F)=CC=4)N(C4CC4)C=3)=O)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.B(O)(O)O.[NH:44]1[CH2:47][CH:46]([NH:48][CH2:49][C@H:50]2[O:54][C:53](=[O:55])[N:52]([C:56]3[CH:57]=[CH:58][C:59]4[S:64][CH2:63][C:62](=[O:65])[NH:61][C:60]=4[CH:66]=3)[CH2:51]2)[CH2:45]1>C(O)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N:44]4[CH2:47][CH:46]([NH:48][CH2:49][C@H:50]5[O:54][C:53](=[O:55])[N:52]([C:56]6[CH:57]=[CH:58][C:59]7[S:64][CH2:63][C:62](=[O:65])[NH:61][C:60]=7[CH:66]=6)[CH2:51]5)[CH2:45]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 66954534HCID 66954534, compoundHCID 89560572HCID 89560572, compound

Product 1

HCID 89561379HCID 89561379, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in analogy to Example 2, starting from 1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid anhydride with boric acid (1:1) and with acetic acid (1:2) (101 mg; prepared according to WO 2010/056633) and 6-[(5R)-5-[(3-azetidinylamino)-methyl]-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (prepared according to WO 2008/126034; 167 mg). At the end of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was taken up in MeOH and treated with 1N HCl in MeOH (3 ml) for 15 min. The reaction mixture was diluted with water (2 ml) and the solid was filtered off. The org. phase was concentrated under reduced pressure and purified by CC (DCM/MeOH 9:1 followed by DCM/MeOH 9:1+1% AcOH), affording after evaporation and stirring of the residue with MeOH/TBME a beige solid.

Workup

  1. customAt the end of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additiontreated with 1N HCl in MeOH (3 ml) for 15 min
  4. additionThe reaction mixture was diluted with water (2 ml)
  5. filtrationthe solid was filtered off
  6. concentrationphase was concentrated under reduced pressure
  7. custompurified by CC (DCM/MeOH 9:1 followed by DCM/MeOH 9:1+1% AcOH)
  8. customaffording
  9. customafter evaporation

Sources & evidence

ORD record
ord-8e8155585e754397ae022456a3615982
Source dataset
uspto-grants-2015_07
Patent number
US09079922B2

Reaction notes

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