Mafenide Hydrochloride → 4-[(3-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide

HRID 1809170Notes

Reaction equation

HRID 1809170 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10](Cl)[C:5]2=[N:4][CH:3]=1.Cl.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=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:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:19][CH:20]=3)[C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 67313Mafenide HydrochlorideHCID 81531DiisopropylethylamineHCID 100598493-Bromo-8-chloroimidazo[1,2-a]pyrazine

Product 1

HCID 583371554-[(3-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
108 °C

Procedure

To a solution of 3-bromo-8-chloro-imidazo[1,2-a]pyrazine (2 g, 8.6 mmol) in iBuOH (5 ml) is added 4-aminomethyl-benzenesulfonamide hydrochloride (2.1 g, 9.5 mmol) and DIPEA (3.7 ml, 21.5 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-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide as a white solid (1.24 g, 38%)

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-cf175d8d049844909162d4a1d62323e6
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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