2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-N-(3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)phenyl)acetamide → CID 78427023

HRID 1050121Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([O:10]CC2C=CC(OC)=CC=2)[N:7]=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]3[O:41][C:42]([CH3:45])=[N:43][N:44]=3)[CH:31]=2)=[O:28])=[C:22]([F:46])[CH:21]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[C:5]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:29][C:30]3[CH:35]=[C:34]([C:36]([F:38])([F:39])[F:37])[CH:33]=[C:32]([C:40]4[O:41][C:42]([CH3:45])=[N:43][N:44]=4)[CH:31]=3)=[O:28])=[C:22]([F:46])[CH:21]=2)=[CH:6][NH:7][C:8](=[O:10])[CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-N-(3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)phenyl)acetamide (60 mg, 0.094 mmol) and Pd/C (10.03 mg, 0.094 mmol) in MeOH (15 mL) was stirred for 0.5 h under a H2 atmosphere at 25° C. Then the mixture was filtered and the filtrate was concentrated to give the residue which was purified by preparative HPLC to yield 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)phenyl)acetamide (41.53 mg, 0.079 mmol, 84% yield): 1H NMR (400 MHz, DMSO-d6) 611.40-11.29 (m, 1H), 10.86 (s, 1H), 8.50 (s, 1H), 8.21 (s, 1H), 7.86 (s, 1H), 7.40-7.29 (m, 2H), 7.23 (d, J=2.6 Hz, 2H), 5.78 (s, 1H), 4.02 (q, J=7.1 Hz, 2H), 3.79 (s, 2H), 2.58 (s, 3H), 1.26 (t, J=6.9 Hz, 3H); ES-LCMS m/z 517 (M+H).

Workup

filtrationThen the mixture was filtered
concentrationthe filtrate was concentrated
customto give the residue which
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-a1dbe8def48441129c056302549f9ea3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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