Dimethylformamide → HCID 68782512, compound

HRID 2266514Notes

Reaction equation

HRID 2266514 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[CH:8]([OH:27])[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[C:10]([CH2:17][CH3:18])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:41](OC(=O)C)([F:43])[F:42]>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:41]([F:43])[F:42])=[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:10]([CH2:17][CH3:18])=[N:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68783448HCID 68783448, compoundHCID 86613376Chlorodifluoromethyl acetate

Product 1

HCID 68782512HCID 68782512, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [8-chloro-2-ethyl-3-(4-fluorobenzyl)-4-hydroxy-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.25 g), N,N-dimethylformamide (1.1 mL), potassium carbonate (0.51 g) and acetic acid chlorodifluoromethyl ester (0.33 mL) was stirred at 70° C. for 16 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts dried over sodium sulfate and then the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane gave title compound, 0.06 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-611fba8597af418f98d01397da29d823
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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