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

HRID 1874492

Reaction equation

HRID 1874492 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]([CH3:10])=[N:3]1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][C:33]=1[Cl:34])[O:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([N:22]=[C:23]([NH:25][C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[N:24]=2)[CH:21]=1>CN(C)C(=O)C>[Cl:34][C:33]1[CH:32]=[CH:31][C:14]([O:15][C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[C:23]([NH:25][C:26]([CH:28]4[CH2:30][CH2:29]4)=[O:27])[N:24]=3)[CH:21]=2)=[CH:13][C:12]=1[NH:11][C:7]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=1)=[O:8]

Participants

4

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 57749285N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749267N-[2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the same manner as in Example 24 and using 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride (89.2 mg, 0.562 mmol), N,N-dimethylacetamide (5 mL) and N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (170 mg, 0.495 mmol) as starting materials, the title compound (92.2 mg, 40%) was obtained as a white solid.

Sources & evidence

ORD record
ord-83f68b8705884beb940dacf50c2bd9b2
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Linked notes

Loading…