Sulfuric Acid → HCID 135931635, compound

HRID 1809175Notes

Reaction equation

HRID 1809175 reaction equation
FC(F)(F)C(O)=[O:4].S(=O)(=O)(O)O.[C:13]([C:15]1[CH:16]=[C:17]([C:22]2[N:26]3[CH:27]=[CH:28][N:29]=[C:30]([NH:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[CH:35][CH:34]=4)[C:25]3=[N:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[OH:21])#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>>[OH:21][C:20]1[CH:19]=[CH:18][C:17]([C:22]2[N:26]3[CH:27]=[CH:28][N:29]=[C:30]([NH:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([S:39](=[O:40])(=[O:41])[NH2:42])=[CH:35][CH:34]=4)[C:25]3=[N:24][CH:23]=2)=[CH:16][C:15]=1[C:13]([NH2:14])=[O:4]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 135931629HCID 135931629, compound

Product 1

HCID 135931635HCID 135931635, compound

Procedure

Trifluoroacetic acid (1.5 ml) and conc. Sulphuric acid (1.5 ml) were added to 4-{[3-(3-cyano-4-hydroxy-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide (0.093 g, 0.2 mmol) and the resulting solution was stirred at ambient temperature for 24 hours. The reaction mixture was neutralized with conc. Aqueous sodium carbonate solution and extracted with ethyl acetate (2×50 mL). The organic layers were combined and dried with magnesium sulphate, filtered and concentrated in vaccuo. The crude material was taken up in DMSO and purified by prep HPLC. The product, 2-hydroxy-5-[8-(4-sulfamoyl-benzylamino)-imidazo[1,2-a]pyrazin-3-yl]-benzamide, is obtained as a white solid (4.2 mg, 5%) (LC-MS m/z 439 [M+H]+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialdried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-74a14105073542aa8425e5b530ffca45
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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