Water → methyl 4-((acetylimino)(3-(3-(4-(N-(4-sulfamoylbenzyl)sulfamoyl)phenyl)ureido)phenyl)methyl)piperazine-1-carboxylate

HRID 1797986Notes

Reaction equation

[NH:1]=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29](=[O:43])(=[O:42])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][CH:33]=3)=[CH:25][CH:24]=2)=[O:21])[CH:14]=1)[N:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[C:53](Cl)(=[O:55])[CH3:54].O>C(Cl)Cl.CN(C=O)C>[C:53]([N:1]=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([S:29](=[O:42])(=[O:43])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([S:38](=[O:41])(=[O:40])[NH2:39])=[CH:34][CH:33]=3)=[CH:27][CH:28]=2)=[O:21])[CH:14]=1)[N:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)(=[O:55])[CH3:54]

Participants

Conditions

Temperature: 0 °C

Procedure

100 mg of compound 60 were dissolved in 2 ml of DCM/DMF 1:1 solution, containing 2 eq of DIEA. Under stirring and at 0° C., 6 eq of acetylchloride were added portionwise during 30 minutes. The solution was stirred overnight at rt, then water was added and a precipitate formed. The precipitate was separated and the title compound was obtained after preparative HPLC purification.

Workup

stirringThe solution was stirred overnight at rt
customa precipitate formed
customThe precipitate was separated

Sources & evidence

ORD record: ord-8bfd9bf696644d6898cdbc850aa1deaf
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343963B2

Reaction notes

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