3-Hydroxybenzoic Acid → HCID 59243104, compound

HRID 1644615Notes

Reaction equation

HRID 1644615 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=O.[CH3:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[C:17](Cl)=O.C(=O)([O-])[O-].[K+].[K+].[Br:26][C:27]1[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[N:31][CH:32]=1>CN(C)C=O.CCOCC>[Br:26][C:27]1[CH:28]=[C:29]2[NH:34][C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([O:1][CH2:17][C:13]4[N:12]([CH3:11])[CH:16]=[CH:15][N:14]=4)[CH:3]=3)=[N:33][C:30]2=[N:31][CH:32]=1

Participants

7

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 6911565-Bromopyridine-2,3-diamineHCID 226467521-Methyl-1H-imidazole-2-carbonyl chloride

Product 1

HCID 59243104HCID 59243104, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzoic acid was reacted with N-methyl-2-imidazoylchloride in the presence of potassium carbonate in dimethylformamide to produce the ether adduct as shown. Subsequent reactions as described previously with 5-bromo-2,3-diaminopyridine followed by microwave reaction gave the final product. 1H NMR (400 MHz, CDCl3) δ ppm 8.37 (s, 1H), 8.09 (s, 1H), 7.84 (s, 1H), 7.35 (m, 3H), 6.95 (m, 1H), 6.87 (m, 1H), 6.73 (m, 1H), 5.30 (s, 2H), 2.25 (s, 3H); Calc'd for C17H14BrN5O; m/z (M+2H+)=385; found 385.

Workup

  1. customfollowed by microwave reaction

Sources & evidence

ORD record
ord-e9a9c8b8534c492a9cd8eec4ec1a5674
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

Loading…