Phthalic Anhydride → HCID 58054415, compound

HRID 1892896Notes

Reaction equation

HRID 1892896 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([NH2:12])=[N:6][NH:7]2.ClC1SC(S(N(S(C2SC(Cl)=CC=2)(=O)=O)C2C3C(=CC=CC=3OC)N(C(OC(C)(C)C)=O)N=2)(=O)=O)=CC=1.[C:50]1(=O)[O:55][C:53](=[O:54])[C:52]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:51]12>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([N:12]1[C:53](=[O:54])[C:52]3[C:51](=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:50]1=[O:55])=[N:6][NH:7]2

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 185260534-Methoxy-1H-indazol-3-amineHCID 580544561,1-dimethylethyl 3-{bis[(5-chloro-2-thienyl)sulfonyl]amino}-4-(methyloxy)-1H-indazole-1-carboxylate

Product 1

HCID 58054415HCID 58054415, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

4-(Methyloxy)-1H-indazol-3-amine (for a preparation see Intermediate 1) (500 mg, 3 mmol) and phthalic anhydride (680 mg, 4.6 mmol) (available from Aldrich) were dissolved in 1,4-dioxane (5 mL) at room temperature. The reaction mixture was stirred at 110° C. overnight, and then it was cooled and concentrated under reduced pressure. The residue was triturated and sonicated with 50 mL of ether. The solid was collected by filtration and dried in a vacuum oven to obtain a brown solid (711 mg, 81%). LCMS (System B) RT=2.82 min, ES+ve m/z 294 (M+H)+.

Workup

  1. temperatureit was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated
  4. customsonicated with 50 mL of ether
  5. filtrationThe solid was collected by filtration
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0a46954bd0b346e0867250c3db430544
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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