2,4,6-Trimethylpyridine → HCID 178522870, compound

HRID 2290038Notes

Reaction equation

HRID 2290038 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][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][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS(Cl)(=O)=O.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]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:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[CH:15][CH:14]=3)=[O:9])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 178522872HCID 178522872, compound

Product 1

HCID 178522870HCID 178522870, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Example No. 166 (1.0 g), collidine (0.45 mL), and DMAP (60.0 mg) in 50 mL anhydrous DMF is cooled to 0° C. Methanesulfonyl chloride (0.25 mL) is added dropwise. The reaction is stirred at room temperature for approx. 2-3 h. Morpholine (0.34 mL) is added. The product is precipitated by addition of H2O. The crude product is adsorbed onto silica and chromatographed eluting with 2% MeOH in CH2Cl2. Fractions homogenous by TLC were combined and condensed to afford 352 mg of the title compound as a white solid.

Workup

  1. customThe product is precipitated by addition of H2O
  2. customchromatographed
  3. washeluting with 2% MeOH in CH2Cl2
  4. customcondensed

Sources & evidence

ORD record
ord-499b97f888c44659b74b28bcb9443a49
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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