Mafenide Hydrochloride → HCID 58337149, compound

HRID 1809181Notes

Reaction equation

HRID 1809181 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10](Cl)[C:5]2=[N:4][C:3]=1[CH3:12].Cl.[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>C(O)C(C)C>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:23])=[O:24])=[CH:20][CH:21]=3)[C:5]2=[N:4][C:3]=1[CH3:12]

Participants

5

Reactant 3

HCID 67313Mafenide HydrochlorideHCID 81531DiisopropylethylamineHCID 58337123HCID 58337123, compound

Product 1

HCID 58337149HCID 58337149, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
108 °C

Procedure

To a solution of 3-bromo-8-chloro-2-methyl-imidazo[1,2-a]pyrazine (0.77 g, 3.12 mmol) in iBuOH (10 ml) is added 4-aminomethyl-benzenesulfonamide hydrochloride (1.04 g, 4.69 mmol) and DIPEA (1.63 ml, 9.36 mmol). The reaction is heated to 108° C. and stirred for 16 h. After this time the solution is allowed to cool, resulting in a thick white precipitate. The precipitate is filtered and washed with diethyl ether to give 4-[(3-Bromo-2-methyl-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulphonamide as a white solid (0.37 g, 30%)

Workup

  1. temperatureto cool
  2. customresulting in a thick white precipitate
  3. filtrationThe precipitate is filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6b75f237f4cd4717ad28fb8b868677a3
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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