Sodium hydride → HCID 8781137, compound

HRID 2217343Notes

Reaction equation

HRID 2217343 reaction equation
[H-].[Na+].Br.[N:4]1[C:8]2[C:9]3[C:14]([CH:15]=[CH:16][C:7]=2[S:6][C:5]=1[NH2:17])=[CH:13][CH:12]=[CH:11][CH:10]=3.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[C:14]([CH:15]=[CH: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)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 87756117HCID 87756117, compound

Product 1

HCID 8781137HCID 8781137, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added sodium hydride (73 mg; 2.89 mmol) to a stirred suspension of 21 (90 mg; 0.27 mmol) in dry tetrahydrofuran under nitrogen at room temperature. After 30 minutes, isonicotinoyl chloride hydrochloride (150 mg; 0.84 mmol) was added and the mixture allowed to stir for 72 hr. at room temperature. The mixture was concentrated in vacuo, the residue taken up into ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried (sodium sulfate), filtered and concentrated in vacuo. Purification using reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid) provided 26 mg of N-Naphtho[1,2-d]thiazol-2-yl-isonicotinamide 22. ES-HRMS m/e calcd for C17H11N3OS (M+H) 306.0696, found 306.0691.

Workup

  1. customat room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. washwashed with saturated ammonium chloride solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-f6934ed02635404ba4d5c11a00ba6b04
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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