Dichloromethane → N-[(4-chlorophenyl)methyl]-1-[(4-chlorophenyl)sulfanylmethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068028Notes

Reaction equation

HRID 1068028 reaction equation
ClC1C=CC(C[C:7]2[C:16]([C:17]([NH2:19])=[O:18])=[C:15]([OH:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:13]=3)[N:8]=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43][CH2:44]Cl)=[CH:39][CH:38]=1.Cl[CH2:47][Cl:48]>CN(C=O)C>[Cl:48][C:47]1[CH:14]=[CH:13][C:12]([CH2:21][NH:19][C:17]([C:16]2[C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[CH:13]=3)[N:8]([CH2:44][S:43][C:40]3[CH:39]=[CH:38][C:37]([Cl:36])=[CH:42][CH:41]=3)[CH:7]=2)=[O:18])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 23610Benzene, 1-chloro-4-((chloromethyl)thio)-HCID 178513551HCID 178513551, compound

Product 1

HCID 16073907N-[(4-chlorophenyl)methyl]-1-[(4-chlorophenyl)sulfanylmethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A suspension of N-(4-chlorobenzyl-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.25 gm) from Preparation No. 40 and cesium carbonate (0.39 gm) in DMF (3 mL) is treated with chloromethyl 4-chlorophenyl sulfide (0.13 mL). The mixture is tightly capped and heated to 105° C. for 2 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane (50 mL), washed with water (2×10 mL), brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 1% to 3% methanol in dichloromethane and then by trituration with ethyl acetate to afford 0.26 gm of the title compound as a white solid.

Workup

  1. customfrom Preparation No
  2. customThe mixture is tightly capped
  3. temperatureto cool to room temperature
  4. washwashed with water (2×10 mL), brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by flash column chromatography
  8. washeluting with 1% to 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-05c6bed423404959bb0ca97049edf8ce
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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