Potassium Carbonate → HCID 78319368, compound

HRID 2280561Notes

Reaction equation

HRID 2280561 reaction equation
Cl[C:2]1[C:3]([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])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[OH:35].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN1C(=O)CCC1.CO>[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[O:35][C:2]1[C:3]([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])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 5930062,4-DimethoxyphenolHCID 86729556HCID 86729556, compound

Product 1

HCID 78319368HCID 78319368, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

To methyl 5-[(3-chloroquinoxaline-2-carbonyl)amino]pyridine-2-carboxylate (51.41 mg, 0.15 mmol) in NMP (1 mL) was added 2,4-dimethoxyphenol (23.12 mg, 0.15 mmol) and potassium carbonate (62.19 mg, 0.45 mmol) and the reaction was heated at 100° C. for 1.5 hours. To the reaction were added 150 μL of MeOH and 150 μL of 3M sodium hydroxide and the reaction was stirred at 50° C. for 1.5 hours. The reaction was cooled to 25° C., 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-(3-(2,4-dimethoxyphenoxy)quinoxaline-2-carboxamido)picolinic acid (26) (26.63 mg, 36%). 1H NMR (400 MHz, DMSO-d6) δ 11.52 (s, 1H), 9.05 (d, J=2.5 Hz, 1H), 8.45 (dd, J=8.6, 2.5 Hz, 1H), 8.18 (dd, J=8.4, 1.6 Hz, 1H), 8.14 (d, J=8.6 Hz, 1H), 7.90-7.71 (m, 3H), 7.22 (d, J=8.7 Hz, 1H), 6.76 (d, J=2.8 Hz, 1H), 6.60 (dd, J=8.8, 2.8 Hz, 1H), 3.81 (s, 3H), 3.68 (s, 3H). ESI-MS m/z calc. 346.12, found 347.2 (M+1)+; Retention time: 1.30 minutes (3 minutes run).

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. filtrationfiltered
  3. custompurified by reverse phase preparative chromatography
  4. additioncontaining HCl as a modifier

Sources & evidence

ORD record
ord-6c0676ddbf9a49018d31b5f5f5bf8a58
Source dataset
uspto-grants-2015_09
Patent number
US09139529B2

Reaction notes

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