Mafenide Hydrochloride → HCID 58337113, compound

HRID 1809188Notes

Reaction equation

HRID 1809188 reaction equation
[Br:1][C:2]1[N:6]2[C:7]([CH3:12])=[CH:8][N:9]=[C:10](Cl)[C:5]2=[N:4][CH:3]=1.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[C:7]([CH3:12])=[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][CH:3]=1

Participants

5

Reactant 3

HCID 67313Mafenide HydrochlorideHCID 81531DiisopropylethylamineHCID 58337160HCID 58337160, compound

Product 1

HCID 58337113HCID 58337113, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
108 °C

Procedure

To a solution of 3-bromo-8-chloro-5-methyl-imidazo[1,2-a]pyrazine (308 mg, 1.25 mmol) in iBuOH (5 mL) is added 4-aminomethyl-benzenesulfonamide hydrochloride (298 mg, 1.38 mmol) and DIPEA (0.43 mL, 3.12 mmol). The reaction is stirred at 108° C. for 16 h. After this time the solution is allowed to cool, resulting in a thick precipitate that is filtered and washed with diethyl ether to give 330 mg of pure product as a beige solid (67%).

Workup

  1. temperatureto cool
  2. customresulting in a thick precipitate that
  3. filtrationis filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-699fdbf22e694b9eb7d011d2ecef6114
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

Loading…