4-Amino-3,5-dichloropyridine → 7-Methoxy-2-methoxymethylfuro[2,3-c]pyridine-4-carboxylic acid (3,5-dichloropyridin-4-yl)amide

HRID 564732Notes

Reaction equation

HRID 564732 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[C:14]3[CH:23]=[C:22]([CH2:24][O:25][CH3:26])[O:21][C:15]=3[C:16]([O:19][CH3:20])=[N:17][CH:18]=2)=[O:12])=CC=1)([O-])=O.[NH2:27][C:28]1[C:33]([Cl:34])=[CH:32][N:31]=[CH:30][C:29]=1[Cl:35]>>[Cl:35][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([Cl:34])[C:28]=1[NH:27][C:11]([C:13]1[C:14]2[CH:23]=[C:22]([CH2:24][O:25][CH3:26])[O:21][C:15]=2[C:16]([O:19][CH3:20])=[N:17][CH:18]=1)=[O:12]

Participants

3

Reactant 2

HCID 898884-Amino-3,5-dichloropyridineHCID 541272917-Methoxy-2-methoxymethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 445623377-Methoxy-2-methoxymethylfuro[2,3-c]pyridine-4-carboxylic acid (3,5-dichloropyridin-4-yl)amideYield 90.8%

Procedure

Starting from 7-methoxy-2-methoxymethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (300 mg) and 4-amino-3,5-dichloropyridine (54 mg). Purification by column chromatography on silica eluting with 1% methanol in dichloromethane gave the title compound (115 mg) as a white solid.

Workup

  1. customPurification by column chromatography on silica eluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-c9549b1e28d040b991441d6d159086bf
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

Loading…