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

HRID 1874444

Reaction equation

HRID 1874444 reaction equation
[NH2:1][C:2]1[N:28]=[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=4)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:4]2[N:3]=1.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1>CN(C)C(=O)C>[CH:29]1([C:32]([NH:1][C:2]2[N:28]=[C:5]3[CH:6]=[CH:7][C:8]([O:10][C:11]4[CH:12]=[C:13]([NH:18][C:19]([C:21]5[N:25]([CH3:26])[N:24]=[C:23]([CH3:27])[CH:22]=5)=[O:20])[CH:14]=[C:15]([CH3:17])[CH:16]=4)=[CH:9][N:4]3[N:3]=2)=[O:33])[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57749338N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 57749346N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-5-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 53%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 28-2 and using N-{3-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (303 mg, 0.803 mmol), cyclopropanecarbonyl chloride (74.0 μL, 0.815 mmol) and N,N-dimethylacetamide (10 mL) as starting materials, the title compound (188 mg, 53%) was obtained as a white solid.

Sources & evidence

ORD record
ord-aebf4e57c2974938bfea9f35beeec54d
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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