HCID 136393283, compound → HCID 86607001, compound

HRID 1868480Notes

Reaction equation

HRID 1868480 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[N:8]2[CH:18]=[C:19]([S:21]([OH:24])(=[O:23])=[O:22])[N:20]=[C:7]2[NH:6][C:5]=1[CH3:25])(=[O:3])[NH2:2]>O1CCOCC1.O=[Mn]=O>[C:1]([C:4]1[C:5]([CH3:25])=[N:6][C:7]2[N:8]([CH:18]=[C:19]([S:21]([OH:24])(=[O:23])=[O:22])[N:20]=2)[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 136393283HCID 136393283, compound

Product 1

HCID 86607001HCID 86607001, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 6-carbamoyl-5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2-sulfonic acid (90 mg, 0.23 mmol) and MnO2 (110 mg, 1.27 mmol) in dioxane (2 mL) was heated to 80° C. for 24 h. HPLC analysis indicated 50% conversion, and additional MnO2 (200 mg) was added and heating was continued for additional 48 h. After removal of catalyst and solvent, 6-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-sulfonic acid was obtained as a brown solid ˜90% pure (75mg, 82%). The crude product was used for the subsequent reaction without further purification.

Workup

  1. additionwas added
  2. temperatureheating
  3. customAfter removal of catalyst and solvent

Sources & evidence

ORD record
ord-e1cdde0c8ded45399aa2916ae4f3a87a
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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