2,4,6-Trimethylpyridine → HCID 178513551, compound

HRID 1067999Notes

Reaction equation

HRID 1067999 reaction equation
ClC1C=CC(C[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])=CC=1.N1[C:30]([CH3:31])=[CH:29][C:28](C)=[CH:27][C:26]=1[CH3:33].CS([Cl:38])(=O)=O.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>CN(C=O)C.CN(C)C1C=CN=CC=1.O>[Cl:38][C:27]1[CH:26]=[CH:33][C:30]([CH2:31][C:11]2[C:10]([C:8]([NH2:7])=[O:9])=[C:19]([OH:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH:17]=3)[N:12]=2)=[CH:29][CH:28]=1

Participants

8

Reactant 4

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

Product 1

HCID 178513551HCID 178513551, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide (1.71 gm) from Preparation No. 9 in DMF (50 mL) at 0° C. under a drying tube is treated with 4-dimethylaminopyridine (0.12 gm), 2,4,6-collidine (1.05 mL) and methanesulfonylchloride (0.60 mL). The mixture is allowed to slowly warm to room temperature overnight. The reaction mixture is then treated with morpholine (8.0 mL) and stirred for 4 hrs. The reaction mixture is poured into water (250 mL) and extracted with dichloromethane (5×50 mL). The combined organic layers are washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by recrystallization from methanol-acetonitrile (1/1, 150 mL) to afford 1.7 gm of the title compound as a white solid.

Workup

  1. extractionextracted with dichloromethane (5×50 mL)
  2. washThe combined organic layers are washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by recrystallization from methanol-acetonitrile (1/1, 150 mL)

Sources & evidence

ORD record
ord-e38e500042244277846022d97c0ccd7a
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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