HCID 59216295, compound → HCID 59216350, compound

HRID 2245941Notes

Reaction equation

HRID 2245941 reaction equation
O.O[CH:3](O)[C:4]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=O.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]3[N:28]([NH2:33])[C:29]([NH2:32])=[N:30][N:31]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(O)(=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]3[N:28]4[N:33]=[C:4]([C:6]5[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=5)[CH:3]=[N:32][C:29]4=[N:30][N:31]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]3[N:28]4[N:33]=[CH:3][C:4]([C:6]5[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=5)=[N:32][C:29]4=[N:30][N:31]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 59216295HCID 59216295, compoundHCID 66812875HCID 66812875, compound

Product 2

HCID 59216350HCID 59216350, compoundHCID 66813099HCID 66813099, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(dihydroxyacetyl)benzoic acid hydrate (0.350 g, 1.63 mmol) and 5-[1-(4-methoxyphenyl)cyclopropyl]-4H-1,2,4-triazole-3,4-diamine (0.245 g, 1.00 mmol, prepared as in Example 16, Steps 1-3) in acetic acid (5.00 mL) was stirred at RT overnight. The solvent was evaporated. The residue was purified by RP-HPLC (pH=10) to give the desired product (isomer I: 33 mg, Rt=1.672 min) and 4-{3-[1-(4-methoxyphenyl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-7-yl}benzoic acid (isomer JJ: 166 mg, Rt=1.747 min.). Analytical LCMS: (M+H)+=388.3.

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-3ff485573e644912a05e8b101e020987
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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