Potassium Carbonate → N-(8H-Indeno[1,2-d]thiazol-2-yl)-isonicotinamide

HRID 2217332Notes

Reaction equation

HRID 2217332 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+].Cl.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=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:21](=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 12262826Isonicotinoyl chloride hydrochloride2×HCID 131876678H-indeno[1,2-d][1,3]thiazol-2-amine

Product 1

HCID 11514840N-(8H-Indeno[1,2-d]thiazol-2-yl)-isonicotinamideYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 8H-Indeno[1,2-d]thiazol-2-ylamine 1b (Prepared in Example 1, Step 2, 640 mg; 3.4 mmol) and potassium carbonate (5.40 g; 39.1 mmol) in dry tetrahydrofuran (20 mL) under nitrogen was added isonicotinoyl chloride hydrochloride (959 mg; 5.10 mmol). The slurry was then heated to reflux for 18 hr. At this point, potassium carbonate (5.40 g; 39.1 mmol) and isonicotinoyl chloride hydrochloride (959 mg; 5.10 mmol) were added and reflux continued for 22 hr., then allowed to cool to room temperature. The solvent was removed in vacuo and the residue diluted with water and extracted with methylene chloride. The insoluble material was filtered off and washed methylene chloride and water and finally triturated with diethyl ether to provide 253 mg of N-(8H-Indeno[1,2-d]thiazol-2-yl)-isonicotinamide 8. EI-HRMS m/e calcd for C16H11N3OS (M+) 293.0623, found 293.0621.

Workup

  1. temperatureThe slurry was then heated
  2. temperatureto reflux for 18 hr
  3. temperaturereflux
  4. customThe solvent was removed in vacuo
  5. additionthe residue diluted with water
  6. extractionextracted with methylene chloride
  7. filtrationThe insoluble material was filtered off
  8. washwashed methylene chloride and water
  9. customfinally triturated with diethyl ether

Sources & evidence

ORD record
ord-bf79244cd829445b89f6b0d76de5eaec
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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