3-Pyridinemethanol → N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(3-pyridylmethyl)methanesulphonamide

HRID 1458555Notes

Reaction equation

HRID 1458555 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[C:15]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[C:16]2[C:21](=[CH:22][C:23]=1[Cl:24])[N:20]=[C:19]([O:25][CH3:26])[C:18]([O:27][CH3:28])=[N:17]2.O[CH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:13][C:14]1[C:15]([N:29]([CH2:35][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)[S:30]([CH3:33])(=[O:32])=[O:31])=[C:16]2[C:21](=[CH:22][C:23]=1[Cl:24])[N:20]=[C:19]([O:25][CH3:26])[C:18]([O:27][CH3:28])=[N:17]2

Participants

6

Reactant 4

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54321377HCID 54321377, compound

Product 1

HCID 22097013N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(3-pyridylmethyl)methanesulphonamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (90 μl, 0.57 mmol) was added to a stirred solution of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)methanesulphonamide (200 mg, 0.57 mmol - see Preparation 3), 3-(hydroxymethyl)pyridine (55 gl, 5 0.57 mmol), and triphenylphosphine (149 mg, 0.57 mmol) in dry tetrahydrofuran (12 ml) under nitrogen at 23° C. After 8 hours, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (gradient elution with ether/methanol) to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(3-pyridylmethyl)methanesulphonamide (145 mg, 57%) as a white solid, m.p. 217° C. (dec.).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (gradient elution with ether/methanol)

Sources & evidence

ORD record
ord-1c4d13f0715647e58ec99b4450357b54
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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