2,4,6-Trimethylpyridine → HCID 178522914, compound

HRID 2290007Notes

Reaction equation

HRID 2290007 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21]O)=[CH:15][C:14]=3[F:23])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS(Cl)(=O)=O.ClC1C=CC(CNC(C2C=NC3C(C=2O)=CC(CCl)=CC=3F)=O)=CC=1.[NH:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][N:65]2[CH2:70][CH2:69][O:68][CH2:67][CH2:66]2)=[CH:15][C:14]=3[F:23])=[O:9])=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 79532,4,6-TrimethylpyridineHCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 178522912HCID 178522912, compoundHCID 178522915HCID 178522915, compound

Product 1

HCID 178522914HCID 178522914, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Example No. 141 (500 mg), collidine (0.21 mL), and DMAP (28.3 mg) in 25 mL DMF is cooled to 0° C. Methanesulfonyl chloride (0.12 mL) is added dropwise. The reaction is stirred at room temperature and monitored by mass spectroscopy for complete conversion to N-(4-chlorobenzyl)-6-(chloromethyl)-8-fluoro-4-hydroxy-3-quinolinecarboxamide (approx. 2-3 hrs and reaction mixture turns yellow). Morpholine (0.24 mL) is added. The reaction is monitored by mass spectroscopy for complete conversion. The product is precipitated by addition of 25 mL H2O. The white solid is filtered and collected to afford 459.3 mg (78%) of the title compound.

Workup

  1. customThe product is precipitated by addition of 25 mL H2O
  2. filtrationThe white solid is filtered
  3. customcollected

Sources & evidence

ORD record
ord-0e93e3894d3344c0a8d7a70e13e36c0c
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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