HCID 85853484, compound → HCID 11540739, compound

HRID 2109398Notes

Reaction equation

FC1C([O:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C:17]#[N:18])[CH:11]=2)=C(F)C(F)=C(F)C=1F.[CH3:24][C:25]1[C:47]([CH3:48])=[CH:46][C:45]([CH3:49])=[C:44]([CH3:50])[C:26]=1[CH2:27][O:28][C:29]1[CH:30]=[C:31]([C:35]2[CH:39]=[CH:38][O:37][C:36]=2[C:40]([NH:42][NH2:43])=[O:41])[CH:32]=[CH:33][CH:34]=1>CN(C=O)C.C(OCC)(=O)C>[C:17]([C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[OH:16])[C:9]([NH:43][NH:42][C:40]([C:36]1[O:37][CH:38]=[CH:39][C:35]=1[C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:27][C:26]2[C:44]([CH3:50])=[C:45]([CH3:49])[CH:46]=[C:47]([CH3:48])[C:25]=2[CH3:24])[CH:30]=1)=[O:41])=[O:8])#[N:18]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-cyano-4-hydroxybenzoic acid pentafluorophenyl ester (compound of Reference Example 63; 0.45 g) and 3-[3-(2,3,5,6-tetramethylbenzyloxy)phenyl]-2-furancarboxylic acid hydrazide (compound of Reference Example 4; 0.50 g) in DMF (5 ml) was stirred at 70° C. overnight. The reaction solution was then diluted with ethyl acetate, washed with 1 M hydrochloric acid and water, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: 0%→10% methanol/chloroform gradient) and recrystallized from ethyl acetate, thereby giving 0.31 g of the desired compound. Melting point: 210-211° C.

Workup

washwashed with 1 M hydrochloric acid and water
dry with materialdried over MgSO4
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: 0%→10% methanol/chloroform gradient)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-79c6c5d2e6be4f7381fce3adb547fc46
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514452B2

Reaction notes

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