Mafenide Hydrochloride → HCID 25205707, compound

HRID 1809199Notes

Reaction equation

HRID 1809199 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Br:14][C:15]1[N:19]2[CH:20]=[C:21]([Br:25])[N:22]=[C:23](Br)[C:18]2=[N:17][CH:16]=1.CCN(C(C)C)C(C)C>C(O)C(C)C>[Br:14][C:15]1[N:19]2[CH:20]=[C:21]([Br:25])[N:22]=[C:23]([NH:2][CH2:3][C:4]3[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=3)[C:18]2=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 67313Mafenide HydrochlorideHCID 81531DiisopropylethylamineHCID 142076223,6,8-Tribromoimidazo[1,2-a]pyrazine

Product 1

HCID 25205707HCID 25205707, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
108 °C

Procedure

4-Aminomethyl-benzenesulfonamide hydrochloride (2.22 g, 10 mmol) was added to a solution of 3,6,8-Tribromo-imidazo[1,2-a]pyrazine (2.77 g, 10 mmol) and DIPEA (3.65 ml, 21 mmol) in iBuOH (20 mL). The reaction was stirred at 108° C. for 3 h then allowed to cool to room temperature. The precipitate formed was filtered and washed with diethyl ether to give 4-[(3,6-Dibromo-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide as a pale brown solid (3.5 g, 76% yield). LC-MS m/z 462 [M+H]+.

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-caa6d8c2b65348b0b99f44fdc78a052d
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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