5-(Hydroxymethyl)furfural → [5-(5-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-furan-2-yl]-methanol

HRID 277059

Reaction equation

HRID 277059 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:22])(=O)=O.[OH:24][CH2:25][C:26]1[O:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1>>[NH2:8][C:6]1[N:5]2[N:22]=[C:30]([C:29]3[O:32][C:26]([CH2:25][OH:24])=[CH:27][CH:28]=3)[N:9]=[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 3

HCID 2373325-(Hydroxymethyl)furfuralHCID 114353934-Bromo-2,6-diaminopyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 18313567[5-(5-Amino-7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-furan-2-yl]-methanol

Procedure

The title compound, MS m/e (%): 311 (M30 +2, 100), was prepared in accordance with the general method of example 63 from 4-bromo-pyridine-2,6-diamine, O-mesitylene-sulfonylhydroxylamine, and 5-hydroxymethyl-furfural. The purification was performed with reversed phase HPLC eluting with an acetonitrile/water gradient.

Sources & evidence

ORD record
ord-7bfc4a57256541d38bf9500f0c0517cf
Source dataset
uspto-grants-2002_03
Patent number
US06355653B1

Linked notes

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