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

HRID 1874507

Reaction equation

HRID 1874507 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][N:5]([CH3:7])[CH:6]=1.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[C:3]([C:8]([NH:22][C:23]2[CH:44]=[CH:43][CH:42]=[C:25]([O:26][C:27]3[CH:28]=[CH:29][C:30]4[N:31]([N:33]=[C:34]([NH:36][C:37]([CH:39]5[CH2:40][CH2:41]5)=[O:38])[N:35]=4)[CH:32]=3)[CH:24]=2)=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 5946854-Chloro-1-methyl-1H-pyrazole-3-carboxylic acidHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 577492904-chloro-N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1-methyl-1H-pyrazole-3-carboxamideYield 45.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 18-4 and using 4-chloro-1-methyl-1H-pyrazole-3-carboxylic acid (156 mg, 0.970 mmol), tetrahydrofuran (7 mL), oxalyl chloride (93.0 μL, 1.07 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.646 mmol), N,N-dimethylformamide (1 drop) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (132 mg, 45%) was obtained as a white solid.

Sources & evidence

ORD record
ord-157815053f0a495cafe6994412546d1d
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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