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

HRID 1874448

Reaktionsgleichung

Reaktionsgleichung von HRID 1874448
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]([OH:9])=O.O1CCCC1.C(Cl)(=O)C(Cl)=O.[NH2:21][C:22]1[CH:23]=[C:24]([CH:41]=[CH:42][CH:43]=1)[O:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([N:32]=[C:33]([NH:35][C:36]([CH:38]3[CH2:40][CH2:39]3)=[O:37])[N:34]=2)[CH:31]=1>CN(C)C=O.CN(C)C(=O)C>[CH:38]1([C:36]([NH:35][C:33]2[N:34]=[C:29]3[CH:28]=[CH:27][C:26]([O:25][C:24]4[CH:23]=[C:22]([NH:21][C:7]([C:6]5[O:5][CH:4]=[N:3][C:2]=5[CH3:1])=[O:9])[CH:43]=[CH:42][CH:41]=4)=[CH:31][N:30]3[N:32]=2)=[O:37])[CH2:39][CH2:40]1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 2923114-Methyl-1,3-oxazole-5-carboxylic acidHCID 57749117N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 57749252N-[3-({2-[(cyclopropylcarbonyl)amino][1,2,4]triazolo[1,5-a]pyridin-6-yl}oxy)phenyl]-4-methyl-1,3-oxazole-5-carboxamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

In the same manner as in Example 18-4 and using 4-methyl-1,3-oxazole-5-carboxylic acid (410 mg, 3.22 mmol), tetrahydrofuran (10 mL), oxalyl chloride (420 μL, 4.84 mmol), N-[6-(3-aminophenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.647 mmol), N,N-dimethylformamide (2 drops) and N,N-dimethylacetamide (10 mL) as starting materials, the title compound (102 mg, 38%) was obtained as a white solid.

Quellen und Nachweise

ORD-Eintrag
ord-5f931befb82d4edf8ec65258922aef67
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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