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

HRID 1874493

Reaktionsgleichung

Reaktionsgleichung von HRID 1874493
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[C:4]([CH3:10])=[N:3]1.O1CCCC1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:22]=[C:23]([CH:40]=[CH:41][C:42]=1[Cl: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:43][C:42]1[CH:41]=[CH:40][C:23]([O:24][C:25]2[CH:26]=[CH:27][C:28]3[N:29]([N:31]=[C:32]([NH:34][C:35]([CH:37]4[CH2:39][CH2:38]4)=[O:36])[N:33]=3)[CH:30]=2)=[CH:22][C:21]=1[NH:20][C:7]([C:5]1[C:4]([CH3:10])=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:8]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 12733041,3-dimethyl-1H-pyrazole-4-carboxylic acidHCID 57749285N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 57749208N-[2-chloro-5-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamideAusbeute 24,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

In the same manner as in Example 55 and using 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (58.2 mg, 0.415 mmol), tetrahydrofuran (5 mL), thionyl chloride (71.7 μL, 0.826 mmol), N,N-dimethylformamide (2 drops), N-[6-(3-amino-4-chlorophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (129 mg, 0.375 mmol) and N,N-dimethylacetamide (6 mL) as starting materials, the title compound (42.5 mg, 24%) was obtained as a white solid.

Quellen und Nachweise

ORD-Eintrag
ord-ec0a5d413a524e67894395e6d680fea3
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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