Dimethylformamide → HCID 22346305, compound

HRID 897360Notes

Reaction equation

HRID 897360 reaction equation
[OH:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([O:14][CH3:15])=[O:13])=[N:4][C:3]=1[C:16]([O:18]C)=O.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH2:28])=[C:23]([S:29][CH3:30])[CH:22]=1.CN(C=O)C>C1(C)C=CC=CC=1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:16]([C:3]2[N:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[C:2]=2[OH:1])=[O:18])=[C:23]([S:29][CH3:30])[CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 167539431-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamineHCID 22346251HCID 22346251, compound

Product 1

HCID 22346305HCID 22346305, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A slurry of dimethyl 8-hydroxy-1,6-naphthyridine-5,7-dicarboxylate (0.25 g, 0.953 mmol), 1-[4-fluoro-2-(methylthio)phenyl]methanamine (0.326 g, 1.91 mmol) and N,N,N-diisopropylethylamine (170 uL, 0.953 mmol) in toluene (4.0 mL) were heated in a pressure tube at 110 degrees C. for 18 hrs. The reaction was incomplete by LCMS analysis and solids remained undissolved. DMF (1 mL) was added to solubilize the reagents and the reaction was again heated in a pressure tube at 110 degrees C. for 18 hrs. Upon cooling to room temperature, the resulting solution was transferred to a round bottom flask and reduced to a small volume. The residue was partitioned between methylene chloride and water. The organic layer was dried with Na2SO4, filtered and reduced in vacuo. The material was crystallized with a small amount of chloroform. The solid was filtered and dried in vacuo to afford the desired compound as a white solid.

Workup

  1. waitfor 18 hrs
  2. temperatureUpon cooling to room temperature
  3. customthe resulting solution was transferred to a round bottom flask
  4. customThe residue was partitioned between methylene chloride and water
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. customThe material was crystallized with a small amount of chloroform
  8. filtrationThe solid was filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-a95db336ab9b49519883259f644cd125
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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