Sodium hydride → HCID 11522637, compound

HRID 2217340Notes

Reaction equation

HRID 2217340 reaction equation
[H-].[Na+].I.[N:4]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH2:10][CH2:9][CH2:8][C:7]=2[S:6][C:5]=1[NH2:18].Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>O1CCCC1>[N:4]1[C:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH2:10][CH2:9][CH2:8][C:7]=2[S:6][C:5]=1[NH:18][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10172205HCID 10172205, compoundHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 11522637HCID 11522637, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added sodium hydride (17 mg; 0.7 mmol) to a stirred suspension of 5,6-Dihydro-4H-3-thia-1-aza-benzo[e]azulen-2-ylamine hydroiodide 17 (80 mg; 0.23 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 1 hr. at room temperature and then concentrated in vacuo. The residue was triturated with water the solid material was filtered off. Purification using reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid) provided 20 mg of N-(5,6-Dihydro-4H-3-thia-1-aza-benzo[e]azulen-2-yl)-isonicotinamide 18 as the trifluoroacetate salt. EI-HRMS m/e calcd for C18H15N3OS (M+) 321.0936, found 321.0935.

Workup

  1. concentrationat room temperature and then concentrated in vacuo
  2. customThe residue was triturated with water the solid material
  3. filtrationwas filtered off
  4. customPurification

Sources & evidence

ORD record
ord-ce636f3c172544a5b39b18c29f3ccff9
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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