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Dichloromethane → N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068031
Notes
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Reaction equation

HRID 1068031 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+].[CH3:36][O:37][CH2:38][CH2:39][O:40][CH2:41]Cl.Cl[CH2:44][Cl:45]>CN(C=O)C>[Cl:45][C:44]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]([CH2:41][O:40][CH2:39][CH2:38][O:37][CH3:36])[CH:7]=2)=[O:18])=[CH:11][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 178513551HCID 178513551, compound

Product 1

HCID 16073911N-[(4-chlorophenyl)methyl]-1-(2-methoxyethoxymethyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A suspension of N-(4-chlorobenzyl-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 and cesium carbonate (0.34 gm) in DMF (2 mL) is treated with 2-methoxyethoxymethyl chloride (0.07 mL). The mixture is tightly capped and heated to 100° C. for 3 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane and washed with water. The aqueous phase is extracted with two additional portions of dichloromethane. The combined organic phase is washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 1% to 5% methanol in dichloromethane and then by recrystallization with acetonitrile to afford 0.08 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
  5. extractionThe aqueous phase is extracted with two additional portions of dichloromethane
  6. washThe combined organic phase is washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product is purified by flash column chromatography
  10. washeluting with 1% to 5% methanol in dichloromethane
  11. customby recrystallization with acetonitrile

Sources & evidence

ORD record
ord-1f30f98ef84040279c17b872b2a3f157
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248739B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes