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

HRID 1874468Notes

Reaction equation

HRID 1874468 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][N:5]([CH3:7])[CH:6]=1.O1CCCC1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][C:42]=1[CH3:43])[O:24][C:25]1[CH:26]=[CH:27][C:28]2[N:29]([N:31]=[C:32]([NH:34][C:35]([CH:37]3[CH2:39][CH2:38]3)=[O:36])[N:33]=2)[CH:30]=1>CN(C)C=O.CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([C:8]([NH:20][C:21]2[CH:22]=[C:23]([O:24][C:25]3[CH:26]=[CH:27][C:28]4[N:29]([N:31]=[C:32]([NH:34][C:35]([CH:37]5[CH2:38][CH2:39]5)=[O:36])[N:33]=4)[CH:30]=3)[CH:40]=[CH:41][C:42]=2[CH3:43])=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 5946854-Chloro-1-methyl-1H-pyrazole-3-carboxylic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 577490984-chloro-N-[5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-2-methylphenyl]-1-methyl-1H-pyrazole-3-carboxamideYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 55 and using 4-chloro-1-methyl-1H-pyrazole-3-carboxylic acid (83.0 mg, 0.519 mmol), tetrahydrofuran (5 mL), thionyl chloride (89.0 μL, 1.02 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.464 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (155 mg, 72%) was obtained as a white solid.

Sources & evidence

ORD record
ord-8ff26c8eebfd4e679af527566b087186
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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