2-Furancarbonyl chloride → (+/-)-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]-2-furancarboxamide

HRID 1827263Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)([C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)[OH:20])[CH:8]=2)[N:3]=1.[O:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[C:39](Cl)=[O:40]>C1COCC1>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:19]([C:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)([OH:20])[C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[CH:8]=3)[N:3]=[C:2]([NH:1][C:39]([C:35]3[O:34][CH:38]=[CH:37][CH:36]=3)=[O:40])[CH:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (±)-2-amino-4-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-6-quinolinemethanol (0.00021 mol), described in International Patent Specification WO 00/39082, and 2-furancarbonyl chloride (0.00063 mol) in THF (1 ml) was heated for 5 hours at 60° C. The solvent was evaporated and the residue was purified by HPLC. The product fractions were collected and the solvent was evaporated, yielding (±)-N-[4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-2-quinolinyl]-2-furancarboxamide, MS (ESI) m/z: 569 571 573.

Workup

customThe solvent was evaporated
customthe residue was purified by HPLC
customThe product fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-91bd9c6890aa47eaaa6770a19afb2834
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053105B2

Reaction notes

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