Sodium hydride → N-(4H-Chromeno[4,3-d]thiazol-2-yl)-isonicotinamide

HRID 2217342Notes

Reaction equation

HRID 2217342 reaction equation
[H-].[Na+].I.[N:4]1[C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[O:15][CH2:16][C:7]=2[S:6][C:5]=1[NH2:17].Cl.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>O1CCCC1>[N:4]1[C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[O:15][CH2:16][C:7]=2[S:6][C:5]=1[NH:17][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 497961204H-Chromeno[4,3-d]thiazol-2-ylamine hydroiodide

Product 1

HCID 11594734N-(4H-Chromeno[4,3-d]thiazol-2-yl)-isonicotinamideYield 14.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added sodium hydride (19 mg; 0.8 mmol) to a stirred suspension of 4H-Chromeno[4,3-d]thiazol-2-ylamine hydroiodide 19 (90 mg; 0.27 mmol) in dry tetrahydrofuran under nitrogen at room temperature. After 15 minutes, isonicotinoyl chloride hydrochloride (62 mg; 0.35 mmol) was added and the mixture allowed to stir for 3 hr. at room temperature and then concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The extracts were dried (sodium sulfate), filtered and concentrated in vacuo. Purification using reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid) provided 12 mg of N-(4H-Chromeno[4,3-d]thiazol-2-yl)-isonicotinamide 20 as the trifluoroacetate salt. ES-HRMS m/e calcd for C16H11N3OS (M+H) 310.0645, found 310.0646.

Workup

  1. concentrationat room temperature and then concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-f3e398764eee4f3f822941e1d79f58d7
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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