Potassium Carbonate → HCID 11522204, compound

HRID 2217333Notes

Reaction equation

HRID 2217333 reaction equation
[S:1]1[C:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[N:3]=[C:2]1[NH2:13].C(=O)([O-])[O-].[K+].[K+].[CH3:20][N:21]1[C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=[N:22]1>O1CCCC1>[S:1]1[C:5]2[CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[N:3]=[C:2]1[NH:13][C:26]([C:25]1[N:21]([CH3:20])[N:22]=[CH:23][CH:24]=1)=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31649321-methyl-1H-pyrazole-5-carbonyl chlorideHCID 131876678H-indeno[1,2-d][1,3]thiazol-2-amine

Product 1

HCID 11522204HCID 11522204, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture 8H-Indeno[1,2-d]thiazol-2-ylamine 1b (Prepared in Example 1, Step 2, 320 mg; 1.70 mmol) and potassium carbonate (3.10 g; 22.4 mmol) in dry tetrahydrofuran (10 mL) under nitrogen was added 2-methyl-2H-pyrazole-3-carbonyl chloride (516 mg; 3.57 mmol). The slurry was then heated to reflux for 3 hr. The solvent was removed in vacuo, and the residue diluted with water and extracted with ethyl acetate. The organic layer was washed with 50 mL of 1N hydrochloric acid solution followed by brine solution and dried (sodium sulfate) filtered and concentrated in vacuo. The crude product was purified by trituration with diethyl ether to provide 155 mg of 2-Methyl-2H-pyrazole-3-carboxylic acid (8H-indeno[1,2-d]thiazol-2-yl)-amide 9. EI-HRMS m/e calcd for C15H12N4OS (M+) 296.0732, found 296.0731.

Workup

  1. temperatureThe slurry was then heated
  2. temperatureto reflux for 3 hr
  3. customThe solvent was removed in vacuo
  4. additionthe residue diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 50 mL of 1N hydrochloric acid solution
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-0e489f83f2ba420390f0c4c5c0621ea3
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

Loading…