Tetrahydrofuran → 5-chloro-N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide

HRID 1874456Notes

Reaction equation

HRID 1874456 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([OH:10])=O.O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:42]=[CH:43][CH:44]=1)[O:26][C:27]1[CH:28]=[CH:29][C:30]2[N:31]([N:33]=[C:34]([NH:36][C:37]([CH:39]3[CH2:41][CH2:40]3)=[O:38])[N:35]=2)[CH:32]=1>CN(C)C=O.CN(C)C(=O)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([NH:22][C:23]1[CH:44]=[CH:43][CH:42]=[C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]3[N:31]([N:33]=[C:34]([NH:36][C:37]([CH:39]4[CH2:40][CH2:41]4)=[O:38])[N:35]=3)[CH:32]=2)[CH:24]=1)=[O:10]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 27357745-Chloro-1-methyl-1H-pyrazole-4-carboxylic acidHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 577491065-chloro-N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideYield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 5-chloro-1-methyl-1H-pyrazole-4-carboxylic acid (291 mg, 1.81 mmol), tetrahydrofuran (10 mL), oxalyl chloride (236 μL, 2.72 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.647 mmol), N,N-dimethylformamide (2 drops) and N,N-dimethylacetamide (10 mL) as starting materials, the title compound (25.0 mg, 9%) was obtained as a white solid.

Sources & evidence

ORD record
ord-16e17546e6bf4728b88d6085063519cb
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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