Hydrochloric Acid → HCID 67520629, compound

HRID 1925365Notes

Reaction equation

HRID 1925365 reaction equation
[F:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][CH:24]=1.Cl>CS(C)=O>[F:1][C:2]1[C:11]([O:12][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH2:36][CH2:37][CH2:38][N:39]4[CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:24]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 222652574-(3-((4-Chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholineHCID 248246045-Fluoro-6-hydroxynaphthalene-1-carboxylic acid

Product 1

HCID 67520629HCID 67520629, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a microwave tube, 5-fluoro-6-hydroxy-1-naphthoic acid (300 mg, 1.48 mmol) and Cs2CO3 (1.45 g, 4.44 mmol) in DMSO (1.5 mL) were stirred for 3 min at RT. 4-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline (500 mg, 1.48 mmol) was added and the vessel sealed. The mixture was subjected to the microwave (Personal Chemistry) at 160° C. for 15 min, then 30 min. The vessel was opened and the mixture stirred with a spatula, resealed and heated another 5 minutes. The reaction mixture made pH 7 with 1N HCl and evaporated. The residual solid was taken up into MeOH and filtered and evaporated. The solid was then taken up into and CH2Cl2/MeOH mixture and filtered. The filtrate was evaporated to dryness and triturated with ethyl acetate/hexanes and the title compound collected as a yellow solid.

Workup

  1. customthe vessel sealed
  2. custom30 min
  3. temperatureheated another 5 minutes
  4. customevaporated
  5. filtrationfiltered
  6. customevaporated
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customtriturated with ethyl acetate/hexanes
  10. customthe title compound collected as a yellow solid

Sources & evidence

ORD record
ord-23521d09672b402a9062cd3353719790
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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