Triethylamine → 2-(6-Aminopyridin-2-yl)-5-{[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1161529Notes

Reaction equation

C([N:3](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[F:25][C:26]1[C:31]([O:32][CH2:33][CH2:34][F:35])=[CH:30][C:29]([O:36][CH3:37])=[CH:28][C:27]=1[CH:38]([NH:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]2[N:65]=[C:64]([CH3:66])[O:63][N:62]=2)=[CH:57][CH:56]=1)[C:39]1[NH:43][C:42](=[O:44])[N:41]([C:45]2[N:50]=[C:49](C(O)=O)[CH:48]=[CH:47][CH:46]=2)[N:40]=1>O1CCOCC1>[NH2:3][C:49]1[N:50]=[C:45]([N:41]2[C:42](=[O:44])[NH:43][C:39]([CH:38]([C:27]3[CH:28]=[C:29]([O:36][CH3:37])[CH:30]=[C:31]([O:32][CH2:33][CH2:34][F:35])[C:26]=3[F:25])[NH:54][C:55]3[CH:60]=[CH:59][C:58]([C:61]4[N:65]=[C:64]([CH3:66])[O:63][N:62]=4)=[CH:57][CH:56]=3)=[N:40]2)[CH:46]=[CH:47][CH:48]=1

Participants

Conditions

Temperature: 80 °C

Procedure

After adding 41 μl of triethylamine and 63 μl of diphenylphosphorylazide to a solution of 81 mg of 6-(3-{[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)pyridine-2-carboxylic acid in 4 ml of 1,4-dioxane under a nitrogen atmosphere, the mixture was heated for 20 hours at 80° C. After cooling, the reaction mixture was filtered and purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give the title compound (33 mg) as a white solid.

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
custompurified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-0ce03795a0ff47da82197dd5f49ccf8f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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