Acetic Acid → HCID 24992460, compound

HRID 1914723Notes

Reaction equation

HRID 1914723 reaction equation
Cl[C:2]1[C:3]([NH:12][S:13]([C:16]2[N:17]=[CH:18][N:19]([CH3:21])[CH:20]=2)(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[NH2:22][C:23]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C(O)(=O)C>O>[CH3:34][O:33][C:31]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([NH:22][C:2]2[C:3]([NH:12][S:13]([C:16]3[N:17]=[CH:18][N:19]([CH3:21])[CH:20]=3)(=[O:15])=[O:14])=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=2)[CH:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12919999Methyl 2-amino-4-methoxybenzoateHCID 57625373HCID 57625373, compound

Product 1

HCID 24992460HCID 24992460, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

N-(3-chloroquinoxalin-2-yl)-1-methyl-1H-imidazole-4-sulfonamide (2 g; 6.2 mmol; 1 eq) and methyl 2-amino-4-methoxybenzoate (1.2 g; 6.8 mmol; 1.1 eq) are taken up in water (60 mL) and acetic acid (160 μL; 3.65 mmol; 0.6 eq) is added. The suspension is heated up to 170° C. in the microwave under normal absorption for 20 min. The reaction is stopped by filtration of the solid and washing with water until neutral. The orange powder obtained is dried under vacuum at 40° C. overnight then taken up in DCM. Triethylamine (1.72 mL) is added. After sonication, the solvents are removed under reduced pressure and the residue obtained is washed with water then dried under vacuum at 40° C. overnight. The powder is taken up in MeOH and refluxed then the suspension is left at 4° C. for 1 h. The precipitate is filtered and washed with MeOH then dried under vacuum at 40° C. for 2 days, to afford 1.68 g (58%) of the title compound as a yellow powder. 1H NMR (DMSO-d6) δ 11.77 (s, 1H), 9.05 (d, J=2.3 Hz, 1H), 8.10-7.95 (m, 2H), 7.90 (s, 1H), 7.85-7.76 (m, 1H), 7.73-7.60 (m, 1H), 7.55-7.35 (m, 2H), 6.73 (dd, J=8.6, 2.2 Hz, 1H), 3.91 (s, 6H), 3.72 (s, 3H). HPLC (max plot) 100%; Rt 4.12 min. LC/MS: (ES+): 469.0, (ES−): 467.1.

Workup

  1. filtrationThe reaction is stopped by filtration of the solid
  2. washwashing with water until neutral
  3. customThe orange powder obtained
  4. customis dried under vacuum at 40° C. overnight
  5. additionTriethylamine (1.72 mL) is added
  6. customAfter sonication
  7. customthe solvents are removed under reduced pressure
  8. customthe residue obtained
  9. washis washed with water
  10. customthen dried under vacuum at 40° C. overnight
  11. temperaturerefluxed
  12. filtrationThe precipitate is filtered
  13. washwashed with MeOH
  14. customthen dried under vacuum at 40° C. for 2 days

Sources & evidence

ORD record
ord-cad0a30e8956458ab56b4bc1c977cb62
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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