Lithium Hydroxide → HCID 90318783, compound

HRID 2280565Notes

Reaction equation

HRID 2280565 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23]C)=[O:22])=[N:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[OH:33].C(=O)([O-])[O-].[K+].[K+].[OH-].[Li+]>CO.CN1CCCC1=O>[ClH:1].[Cl:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[O:33][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[N:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 3939Lithium Hydroxide2×HCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 86729558HCID 86729558, compound

Product 1

HCID 90318783HCID 90318783, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To methyl 5-(2-chloroquinoline-3-carboxamido)picolinate (52.26 mg, 0.15 mmol), 2-chloro-4-fluorophenol (21.98 mg, 0.15 mg), potassium carbonate (62.19 mg, 0.45 mmol) and 1-methylpyrrolidin-2-one (1 mL) were added and the reactions were stirred at 100° C. for 1 hour. 2M lithium hydroxide (75 μL, 0.45 mmol) and methanol (150 μL) were added and the reaction stirred at 50° C. for 2 hours. The reaction was filtered and (75 μL, 0.45 mmol) of 2M lithium hydroxide were added and stirring was continued for an additional 2 hours. The reaction was filtered and purified by reverse phase preparative chromatography utilizing a gradient of 10-99% acetonitrile in water containing HCl as a modifier to yield 5-(2-(2-chloro-4-fluorophenoxy)quinoline-3-carboxamido)picolinic acid hydrochloric acid (79) (4.2 mg, 6%). ESI-MS m/z calc. 437.06, found 338.4 (M+1)+)+; Retention time: 1.49 minutes (3 minutes run).

Workup

  1. stirringthe reaction stirred at 50° C. for 2 hours
  2. filtrationThe reaction was filtered
  3. stirringstirring
  4. waitwas continued for an additional 2 hours
  5. filtrationThe reaction was filtered
  6. custompurified by reverse phase preparative chromatography
  7. additioncontaining HCl as a modifier

Sources & evidence

ORD record
ord-c79fcf8da2464ec596375a30701cf74f
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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