Mafenide Hydrochloride → HCID 58659649, compound

HRID 1676986Notes

Reaction equation

ClC1C=C2C(=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.[Br:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35](S(C1C=CC=CC=1)(=O)=O)[C:34]([C:48]([O:50]CC)=O)=[C:33]2[S:53](Cl)(=[O:55])=[O:54].Cl.CN.Cl.[NH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([S:69]([NH2:72])(=[O:71])=[O:70])=[CH:65][CH:64]=1>>[NH2:72][S:69]([C:66]1[CH:65]=[CH:64][C:63]([CH2:62][NH:61][S:53]([C:33]2[C:32]3[C:36](=[CH:37][CH:38]=[C:30]([Br:29])[CH:31]=3)[NH:35][C:34]=2[C:48]([NH2:7])=[O:50])(=[O:54])=[O:55])=[CH:68][CH:67]=1)(=[O:70])=[O:71]

Participants

Reactant 4

HCID 67313Mafenide Hydrochloride

HCID 6364545Methylamine hydrochloride

HCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 58659649HCID 58659649, compound

Procedure

Following the procedures described in Steps D and E of Example 1, replacing in Step D ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and methylamine hydrochloride with 4-(aminomethyl)benzene-sulfonamide hydrochloride, the title compound was obtained. HRMS (ES) exact mass calculated for C16H16BrN4O5S2 (M+H+): 486.9740. Found 486.9749.

Sources & evidence

ORD record: ord-2b22f406a48b4dcbb243e5d6af76c4af
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008295B2

Reaction notes

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