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

HRID 1874432

Reaction equation

HRID 1874432 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([CH:23]=1)[O:7][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([N:14]=[C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[N:16]=2)[CH:13]=1.[CH3:25][N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([CH3:34])=[N:27]1>CN(C)C(=O)C>[CH:20]1([C:18]([NH:17][C:15]2[N:16]=[C:11]3[CH:10]=[CH:9][C:8]([O:7][C:6]4[CH:23]=[C:2]([NH:1][C:31]([C:30]5[N:26]([CH3:25])[N:27]=[C:28]([CH3:34])[CH:29]=5)=[O:32])[CH:3]=[CH:4][C:5]=4[CH3:24])=[CH:13][N:12]3[N:14]=2)=[O:19])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57749340N-[6-(3-amino-6-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749237N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)-4-methylphenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 24 and using N-[6-(5-amino-2-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (265 mg, 0.820 mmol), 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (260 mg, 1.64 mmol) and N,N-dimethylacetamide (5 mL) as starting materials, the title compound (333 mg, 91%) was obtained as a white solid.

Sources & evidence

ORD record
ord-a9ab00f959154b7fa90fe11ecc6db157
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

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