Sodium hydride → HCID 861854, compound

HRID 2217338Notes

Reaction equation

HRID 2217338 reaction equation
[H-].[Na+].I.[N:4]1[C:8]2[C:9]3[C:14]([CH2:15][CH2:16][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]([CH2:15][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)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 49796118HCID 49796118, compound

Product 1

HCID 861854HCID 861854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added sodium hydride (26 mg; 1.1 mmol) to a stirred suspension of 4,5-Dihydro-naphtho[1,2-d]thiazol-2-ylamine hydroiodide 15 in dry tetrahydrofuran under nitrogen at room temperature. After 15 minutes, isonicotinoyl chloride hydrochloride (107 mg; 0.60 mmol) was added and the mixture allowed to stir for 2 hr. at room temperature and then concentrated in vacuo. The residue was diluted 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-(4,5-Dihydro-naphtho[1,2-d]thiazol-2-yl)-isonicotinamide 16 as the trifluoroacetate salt. ES-HRMS m/e calcd for C17H13N3OS (M+H) 308.0852, found 308.0851.

Workup

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

Sources & evidence

ORD record
ord-64aed7b35a39484a9ec9eb521ecd014c
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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