Trifluoroacetic acid → N-[6-(3-amino-4-fluorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 1874477Notes

Reaction equation

HRID 1874477 reaction equation
[NH2:1][C:2]1[N:26]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[CH:13][C:14]([F:25])=[C:15]([NH:17]C(=O)OC(C)(C)C)[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1.FC(F)(F)C(O)=O>CN(C)C(=O)C>[NH2:17][C:15]1[CH:16]=[C:11]([CH:12]=[CH:13][C:14]=1[F:25])[O:10][C:8]1[CH:7]=[CH:6][C:5]2[N:4]([N:3]=[C:2]([NH:1][C:30]([CH:27]3[CH2:29][CH2:28]3)=[O:31])[N:26]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 77637Cyclopropanecarbonyl chlorideHCID 57749150HCID 57749150, compound

Product 1

HCID 57749270N-[6-(3-amino-4-fluorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 66-2 and using tert-butyl {5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-fluorophenyl}carbamate (8.99 g, 25.0 mmol), cyclopropanecarbonyl chloride (3.82 mL, 42.0 mmol), N,N-dimethylacetamide (60 mL) and trifluoroacetic acid (50 mL) as starting materials, the title compound (6.32 g, 77%) was obtained as a white solid.

Sources & evidence

ORD record
ord-0470f920995c43258535760dbf733e3a
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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