Triethylamine → 3-Fluoro-N-(5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide

HRID 2120760Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([NH2:12])[N:11]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.[F:19][C:20]1[CH:21]=[C:22]([C:26](Cl)=[O:27])[CH:23]=[CH:24][CH:25]=1.CCN(CC)CC>O1CCOCC1>[F:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[C:26]([NH:12][C:10]1[N:11]=[C:7]2[C:6]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]2[N:9]=1)=[O:27]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 15 mg (0.062 mmol) 5-methoxy-8-phenyl-[1,2,4]triazolo[1,5-a]-pyridin-2-yl-amine, 11 mg (0.068 mmol) 3-fluorophenyl carboxylic acid chloride, and 31.5 μl (0.312 mmol) NEt3 in 1 ml dioxane was heated to 90° C. for 16 h. The mixture was purified by preparative HPLC on reversed phase eluting with an acetonitrile/water gradient. Evaporation yielded the title compound. MS m/e (%): 281.7 ((M+CH3CN)+, 100).

Workup

customThe mixture was purified by preparative HPLC on reversed phase
washeluting with an acetonitrile/water gradient
customEvaporation

Sources & evidence

ORD record: ord-fec5e731dd0f4763b31afdf04ea3321b
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693116B2

Reaction notes

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