Hydrochloric Acid → HCID 56598479, compound

HRID 535468Notes

Reaction equation

HRID 535468 reaction equation
Cl.CN.[B-](F)(F)(F)F.CCOC([C:14](C#N)=[N:15]OC(N(C)C)=[N+](C)C)=O.CCN(C(C)C)C(C)C.[CH3:35][O:36][C:37]1[C:38]([CH3:62])=[C:39]([C:46]([C:48]2[CH:49]=[C:50]3[C:55](=[CH:56][CH:57]=2)[NH:54][CH:53]=[C:52]([C:58]([OH:60])=O)[C:51]3=[O:61])=[O:47])[N:40]2[C:45]=1[CH:44]=[CH:43][CH:42]=[CH:41]2.Cl>CN(C=O)C>[CH3:35][O:36][C:37]1[C:38]([CH3:62])=[C:39]([C:46]([C:48]2[CH:49]=[C:50]3[C:55](=[CH:56][CH:57]=2)[NH:54][CH:53]=[C:52]([C:58]([NH:15][CH3:14])=[O:60])[C:51]3=[O:61])=[O:47])[N:40]2[C:45]=1[CH:44]=[CH:43][CH:42]=[CH:41]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6364545Methylamine hydrochloride2×HCID 66653201HCID 66653201, compound

Product 1

HCID 56598479HCID 56598479, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.36 g (5.31 mmol) of methylamine hydrochloride, 1.3 g (3.99 mmol) of TOTU and 1.37 g (10.63 mmol) of DIEA are added to 1 g (2.66 mmol) of 6-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid in 23 ml of anhydrous DMF. The reaction medium is stirred at ambient temperature under a nitrogen atmosphere for 8 h. 0.36 g (5.33 mmol) of methylamine hydrochloride is added to the reaction medium. After 18 h at ambient temperature, the reaction medium is hydrolysed with a 1N solution of HCl and then extracted with ethyl acetate. The organic phase is washed with a saturated solution of sodium chloride, dried over sodium sulphate, and then concentrated under reduced pressure. The residue obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (90/10) mixture. 0.06 g of a yellow solid is obtained.

Workup

  1. waitAfter 18 h at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-5ff87fd82f9a458d9f855e273abd838e
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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