HCID 135825031, compound → HCID 135486052, compound

HRID 1166241Notes

Reaction equation

HRID 1166241 reaction equation
[CH2:1]([C:4]1[C:5]([OH:23])=[C:6]([N:11]2[C:15](=[O:16])[NH:14][C:13]([C:17]3[S:18][C:19](Br)=[CH:20][CH:21]=3)=[N:12]2)[CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:2]=[CH2:3]>C(O)C.[Pt]>[Cl:10][C:8]1[CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]([OH:23])=[C:6]([N:11]2[C:15](=[O:16])[NH:14][C:13]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[N:12]2)[CH:7]=1

Participants

4

Reactant 1

HCID 135825031HCID 135825031, compound

Product 1

HCID 135486052HCID 135486052, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-(3-Allyl-5-chloro-2-hydroxyphenyl)-5-(5-bromothiophen-2-yl)-2,4-dihydro-[1,2,4]triazol-3-one (Compound of Example 20) (206 mg) and 10%Pt(S)/C (206 mg) in ethanol (8 ml) was hydrogenated at 50 psi for 3 hours. After filtration and concentration, the residue was purified to give 50 mg (30%) of 2-(5-chloro-2-hydroxy-3-propylphenyl)-5-(thiophen-2-yl)-2,4-dihydro-[1,2,4]triazol-3-one. 1H NMR (300 MHz, DMSO-d6) δ12.9 (s, 1 H), 9.56 (s, 1 H), 7.79 (dd, J=4.89, 0.9 Hz, 1 H), 7.31 (d, J=2.6 Hz, 1 H), 7.23-7.21 (m, 2 H), 2.61 (t, J=7.4 Hz, 2 H), 1.64 (m, 2 H), 0.94 (t, J=7.2 Hz, 2 H); 13C NMR (75 MHz, DMSO-d6) δ153.9, 147.9, 142.8, 133.7, 129.4, 129.0, 128.5, 128.3, 125.6, 123.0, 122.6, 31.8, 22.4,13.9; IR (KBr, cm−1) 1701; MS(ESI) 334 (M−1)−.

Workup

  1. filtrationAfter filtration and concentration
  2. customthe residue was purified

Sources & evidence

ORD record
ord-396f450de95d4ee69792097d8426da30
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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