HCID 67392406, compound → HCID 44476497, compound

HRID 908670Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:22])[CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:19](=[O:20])[C:14]2[N:15]=[C:16]([CH3:18])[S:17][C:13]=2[C:12](=[O:21])[CH:11]=1.CO[C:25]1[C:44](=[O:45])[C:29]2[N:30]=[C:31]([C:33]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)=[O:34])[S:32][C:28]=2[C:27](=[O:46])[CH:26]=1>C(O)C>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([NH:35][C:33]([C:31]2[S:32][C:28]3[C:27](=[O:46])[CH:26]=[C:25]([NH:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:22])[CH2:6][CH2:7][CH2:8][NH:9][C:10]4[C:19](=[O:20])[C:14]5[N:15]=[C:16]([CH3:18])[S:17][C:13]=5[C:12](=[O:21])[CH:11]=4)[C:44](=[O:45])[C:29]=3[N:30]=2)=[O:34])=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-({3-[(3-aminopropyl)(methyl)amino]propyl}amino)-2-methyl-1,3-benzothiazole-4,7-dione is solubilized in 250 ml of ethanol and 2.12 g (6.16 mmol; 0.8 equivalent) of 5-methoxy-N-(4-methoxyphenyl)-4,7-dioxo-4,7-dihydro-1,3-benzothiazole-2-carboxamide is added. The reaction mixture is maintained under stirring at 60° C. for 4 hours, then the solvent is evaporated off under reduced pressure. The residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5) and 450 mg (yield=9%) of N-(4-methoxyphenyl)-5-{[3-(methyl{3-[(2-methyl-4,7-dioxo-4,7-dihydro-1,3-benzothiazol-5-yl)amino]propyl}amino)propyl]amino}-4,7-dioxo-4,7-dihydro-1,3-benzothiazole-2-carboxamide is obtained in the form of red powder.

Workup

temperatureThe reaction mixture is maintained
customthe solvent is evaporated off under reduced pressure
customThe residue is then purified by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5)

Sources & evidence

ORD record: ord-2fbccc395f3a4f5a8bd725df1048cb9b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017637B2

Reaction notes

Loading…