HCID 19603302, compound → HCID 178422702, compound

HRID 1604606Notes

Reaction equation

[Cl:1][C:2]1[C:20]([N:21]([CH3:37])[C:22](=[O:36])[CH2:23][NH:24][C:25](=[O:35])[CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:19][CH:18]=[C:17]([Cl:38])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.C(OC([N:46]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:47](=[NH:51])SOC)=O)(C)(C)C>C(O)C.[Hg]=O>[Cl:1][C:2]1[C:20]([N:21]([C:22](=[O:36])[CH2:23][NH:24][C:25](=[O:35])[CH:26]=[CH:27][C:28]2[CH:29]=[CH:30][C:31]([NH:34][C:47]([NH:46][C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])=[N:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[CH:32][CH:33]=2)[CH3:37])=[CH:19][CH:18]=[C:17]([Cl:38])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

Conditions

Temperature: 40 °C

Procedure

to asolution of 8-[2,6-dichloro-3-[N-methyl-N-(4-aminocinnamoylglycyl)amino]benzyloxy]-2-methylquinoline (50 mg) in ethanol (2 ml) were added N,N-bis(tert-butoxycarbonyl)-S-methoxyisothiourea (28 mg) and mercury (II) oxide (21 mg) at ambient temperature and stirred for 1 hours at 40° C. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (8% solution of methanol in chloroform) to give 8-[2,6-dichloro-3-[N-[4-[2,3-bis(tert-butoxycarbonyl)guanidino]-cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylquinoline (60 mg) as an amorphous powder.

Workup

filtrationThe reaction mixture was filtered
customthe filtrate was evaporated in vacuo
customThe residue was purified by preparative thin-layer chromatography (8% solution of methanol in chloroform)

Sources & evidence

ORD record: ord-16b98e155aa04cc387fd8df3bfb076bf
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994368

Reaction notes

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